StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
Huagongshe Open Project:[email protected]KI-Anbindung: llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.7.8
  1. Startseite
  2. /Verbindung

Maslinic Acid

HCID 73659
NotizenReaktionen
GrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
TeilstruktursucheÄhnliche Strukturen suchen

Grundinformationen

CAS
4373-41-5
Standard-SMILES
CC1(C)CC[C@]2(C(=O)O)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)C[C@@H](O)[C@H](O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]2C1
InChIKey
MDZKJHQSJHYOHJ-LLICELPBSA-N
Summenformel
C30H48O4
Durchschnittliche Molmasse
472,7 g/mol
Monoisotopische Masse
472,35526001

Überblick

Maslinic acid is a pentacyclic triterpenoid that is olean-12-ene substituted by hydroxy groups at positions 2 and 3 and a carboxy group at position 28 (the 2alpha,3beta stereoisomer). It is isolated from Olea europaea and Salvia canariensis and exhibits anti-inflammatory, antioxidant and antineoplastic activity. It has a role as an antioxidant, an antineoplastic agent, an anti-inflammatory agent and a plant metabolite. It is a pentacyclic triterpenoid and a dihydroxy monocarboxylic acid. It derives from a hydride of an oleanane.

Namen und Bezeichner

Bevorzugter Name
Maslinic Acid
IUPAC
(4aS,6aR,6aS,6bR,8aR,10R,11R,12aR,14bS)-10,11-dihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
Englischer Name
Maslinic acid
Summenformel
C30H48O4
Molmasse
472.7

Namen und Synonyme

Maslinic acid4373-41-5Crategolic acidCrataegolic acidMaslic acidMasilinic acid2alpha-hydroxyoleanolic acid(4aS,6aR,6aS,6bR,8aR,10R,11R,12aR,14bS)-10,11-dihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acidE233J88OHQ2alpha,3beta-dihydroxyurs-12-en-29-oic acid2-hydroxyoleanolic acidCHEBI:66682
Weitere Namen anzeigen
2α-Hydroxyoleanolic acidMasLCrataegic acidmaslinicaciMasalic acidHawthorn acidMaslinic acid-RM
DTXSID30905074(2alpha, 3beta)-2,3-dihydroxyolean-12-en-28-oic acid(2beta, 3alpha)-2,3-dihydroxyolean-12-en-28-oic acidOlean-12-en-28-oic acid, 2,3-dihydroxy-, (2alpha,3beta)-RefChem:41765(2alpha, 3beta)-2,3-dihydroxy-olean-12-en-28-oic acidDTXCID101334176olean-12-en-28-oic acid, 2,3-dihydroxy-, (2alpha, 3beta)-

Datenbank-Bezeichner

CAS
4373-41-5
PubChem CID
73659
DTXSID
DTXSID30905074
ChEMBL
CHEMBL201515
ChEBI
CHEBI:66682
UNII
E233J88OHQ
EC Number
610-137-3
Nikkaji
J22.580K

Eigenschaften

Berechnete Struktureigenschaften

XLogP
6,5
Polarare Oberfläche (TPSA)
77,8 Ų
H-Brücken-Donoren
3
H-Brücken-Akzeptoren
4
Frei drehbare Bindungen
1
Schwere Atome
34
Formalladung
0
Komplexität
919

Experimentelle und physikochemische Eigenschaften

LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C30 isoprenoids (triterpenes) [PR0106]
Density1.15 g/cu cm
Color/FormCrystalline solid
Solubility · 3 Einträge

Solubility of 0.3 mg/mL in a 1:2 solution of Ethanol:Buffered Water (pH 7.2) at 25 °C

In ethanol: 0.5 mg/mL; in DMSO: 20 mg/mL; in dimethyl formamide: 15 mg/mL

Sparingly soluble in aqueous buffers

Melting Point249 - 250 °C
Physical DescriptionSolid

Physikochemische Eigenschaften

Schmelzpunkt
267 · 267~269℃
Siedepunkt
570 · 570.0±50.0 °C(Predicted)
Dichte
1.14 · 1.14±0.1 g/cm3(Predicted)
storage temp.
2 · 2-8°C
Löslichkeit
1 mg/mL, · acetone: soluble1mg/mL, clear, colorless
pka
4.63 · 4.63±0.70(Predicted)
Aggregatzustand
powder
Farbe
white to off-white
Henry's Law Constant
2.8 · 2.8×105 mol/(m3Pa) at 25℃, HSDB (2015)
Stabilität
Hygroscopic
Major Application
food and beverages
Kosmetik-Inhaltsstoffe Funktionen
SKIN CONDITIONINGANTIOXIDANT
InChIKey
MDZKJHQSJHYOHJ-LLICELPBSA-N
SMILES
[C@@]12(C)CC[C@@]3([H])C(C)(C)[C@@H](O)[C@H](O)C[C@]3(C)[C@@]1([H])CC=C1[C@]3([H])CC(CC[C@]3(C(=O)O)CC[C@@]21C)(C)C |&1:0,4,9,11,14,16,21,27,33,r|
LogP
7.87 · 7.870 (est)

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

Sicherheit und Schutzausrüstung

Fire Fighting Procedures · 2 Einträge

As in any fire, wear self-contained breathing apparatus pressure-demand (MSHA-NIOSH approved or equivalent), and full protective gear to prevent contact with skin and eyes.

Use alcohol-resistant foam, carbon dioxide, water, or dry chemical spray when fighting fires involving this material.

Cleanup Methods · 1 Eintrag

Steps to be taken in case material is released or spilled: Wear a NIOSH/MSHA approved self-contained breathing apparatus and appropriate personal protection (rubber boots, safety goggles, and heavy rubber gloves). Vacuum or sweep up material and place in disposal container. Avoid breathing dust. After removal, ventilate contaminated area and flush thoroughly with water.

Disposal Methods · 2 Einträge

SRP: Criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.

Preventive Measures · 2 Einträge

Wash thoroughly after handling.

SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. The completeness of the cleaning procedures should be considered before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at the end of shift, but should remain at employee's place of work for cleaning.

Personal Protective Equipment (PPE) · 3 Einträge

Safety glasses, latex disposable gloves

Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower.

Use process enclosures, local exhaust ventilation, or other engineering controls to control airborne levels below recommended exposure limits.

Toxikologische Informationen

Environmental Fate · 3 Einträge

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1270(SRC), determined from an estimated log Kow of 6.82(2) and a regression-derived equation appropriate for ionizable compounds(2), indicates that maslinic acid is expected to have low mobility in soil(SRC). The estimated pKa of maslinic acid is 4.81(3), indicating that this compound will exist partially in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization of maslinic acid from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.5X10-11 atm-cu m/mole(SRC) using a fragment constant estimation method(2). Maslinic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.3X10-15 mm Hg at 25 °C(SRC) determined from a fragment constant method(2). Biodegradation data in soil were not available(SRC, 2012).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1270(SRC), determined from an estimated log Kow of 6.82(2) and a regression-derived equation appropriate for ionizable compounds(2), indicates that maslinic acid is expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 3.5X10-11 atm-cu m/mole(SRC) developed using a fragment constant estimation method(2). According to a classification scheme(4), an estimated BCF of 56(SRC), from an estimated log Kow of 6.82(2) and a regression-derived equation(2), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Maslinic acid is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(3). Maslinic acid contains a cyclic olefin and cyclic olefins can undergo sensitized photo-oxidation in surface waters exposed to sunlight via reaction with hydroxyl, singlet oxygen and RO2 radicals with half-lives on the order of 13 to 40 days at the water surface(5); therefore, photo-oxidation may be an important fate process for maslinic acid in natural water(SRC). Biodegradation data in water were not available(SRC, 2012).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), maslinic acid, which has an estimated vapor pressure of 2.3X10-15 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase maslinic acid may be removed from the air by wet and dry deposition(SRC).

Plant Concentrations · 3 Einträge

Maslinic acid is widely distributed in plants, being particularly abundant in the surface wax on the fruits and leaves of Olea europaea(1). Maslinic acid occurs in red dates, olives, camellia, megranate and sage(2). The concentration of maslinic acid in olive oil increases as the quality of the olive oil decreases(3); maslinic acid concentrations in olive oil were found to be 38 mg/kg for extra virgin, 227 mg/kg for a 9.3%-acidity virgin oil and 721 mg/kg for crude pomace olive oil(3).

Maslinic acid detections in various plants(1).[Table#8079]

The occurrence of triterpene pentacyclic acids in plants is extensive, but little is known about their availability in commercial extracts. A simple GC-MS method for the simultaneous determination of betulinic, corosolic, maslinic, oleanolic and ursolic acids was developed and applied to 38 different commercial plant extracts sold as ingredients for dietary supplements. ... Lagerstroemia speciosa was rich in maslinic acid (4958 mg/kg) ... Lower quantities of triterpenic acids were identified in dried extracts of Harpagophyton procumbens root, propolis, Punica granatum root, Styrax benzoin, Vaccinium myrtillus fruits and Vitis vinifera seeds. Decoctions and fluid extracts lacked or contained very low amounts of triterpenic acids. ...

Soil Adsorption/Mobility · 1 Eintrag

The Koc of maslinic acid is estimated as 1270(SRC), using an estimated log Kow of 6.82(1) and a regression-derived equation appropriate for an ionizable compound(1). According to a classification scheme(2), this estimated Koc value suggests that maslinic acid is expected to have low mobility in soil. The estimated pKa of maslinic acid is 4.81(3), indicating that this compound will exist partially in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4).

Natural Pollution SourcesMaslinic acid is found in a number of natural sources, most notably pomace olive oil (orujo)(1). Maslinic acid occurs in red dates, olives, camellia, pomegranate and sage(2).
Human Toxicity Excerpts · 5 Einträge

/ALTERNATIVE and IN VITRO TESTS/ Olives and their derivatives represent an important component of the Mediterranean diet that has been considered to be protective against cancer... the effect on cell proliferation and apoptosis in HT-29 cells of an extract from the skin of olives composed of pentacyclic triterpenes with the main components maslinic acid (73.25%) and oleanolic acid (25.75%) was investigated. Studies of the dose-dependent effects showed antiproliferative activity at an EC50 value of 73.96 +/- 3.19 uM/L of maslinic acid and 26.56 +/- 2.55 uM/L of oleanolic acid without displaying necrosis. Apoptosis was confirmed by the microscopic observation of changes in membrane permeability in 40.9 +/- 3.9% and detection of DNA fragmentation in 24.5 +/- 1.5% of HT-29 cells incubated for 24 hr with olive fruit extract containing 150 and 55.5 uM/L of maslinic and oleanolic acids, respectively. Caspase-3 was activated in a dose-dependent manner after incubation for 24 hr. The extract containing 200 uM/L maslinic acid and 74 uM/L oleanolic acid increased caspase-3-like activity to 6-fold that of control cells. Programmed cell death was induced by the intrinsic pathway, as evidenced by the production of superoxide anions in the mitochondria of cells treated with olive fruit extracts containing 150 and 55.5 uM/L of maslinic and oleanolic acids, respectively...

/ALTERNATIVE and IN VITRO TESTS/ Protein kinase C (PKC) has been implicated in carcinogenesis and displays variable expression profiles during cancer progression. Studies of dietary phytochemicals on cancer signaling pathway regulation have been conducted to search for potent signaling regulatory agents. The present study was designed to evaluate any suppressive effect of maslinic acid on PKC expression in human B-lymphoblastoid cells (Raji cells), and to identify the PKC isoforms expressed. Effects of maslinic acid on PKC activity were determined using a PepTag assay for non-radioactive detection of PKC. The highest expression in Raji cells was obtained at 20 nM PMA induced for 6 hours. Suppressive effects of maslinic acid were compared with those of four PKC inhibitors (H- 7, rottlerin, sphingosine, staurosporine) and two triterpenes (oleanolic acid and ursolic acid). The IC50 values achieved for maslinic acid, staurosporine, H-7, sphingosine, rottlerin, ursolic acid and oleanolic acid were 11.52, 0.011, 0.767, 2.45, 5.46, 27.93 and 39.29 uM, respectively. Four PKC isoforms, PKC beta I, beta II, delta, and zeta were identified in Raji cells via western blotting. Maslinic acid suppressed the expression of PKC beta I, delta, and zeta in a concentration-dependent manner. These preliminary results suggest promising suppressive effects of maslinic acid on PKC activity in Raji cells. Maslinic acid could be a potent cancer chemopreventive agent that may be involved in regulating many downstream signaling pathways that are activated through PKC receptors.

/ALTERNATIVE and IN VITRO TESTS/Tumor necrosis factor alpha (TNFalpha) has been used to treat certain tumors in clinic/al/ trials. However, the curative effect of TNFalpha has been undermined by the induced-NF-kappa B activation in many types of tumor. Maslinic acid (MA), a pharmacological/ly/ safe natural product, has been known for its important effects as anti-oxidant, anti-inflammatory, and anti-viral activities. The aim of this study was to determine whether MA potentiates the anti-tumor activity of TNFalpha though the regulation of NF-kappaB activation. /This study demonstrates/ that MA significantly enhanced TNFalpha-induced inhibition of pancreatic cancer cell proliferation, invasion, and potentiated TNFalpha-induced cell apoptosis by suppressing TNFalpha-induced NF-kappa B activation in a dose- and time-dependent manner. Addition of MA inhibited TNFalpha-induced I kappa B alpha degradation, p65 phosphorylation, and nuclear translocation. Furthermore, MA decreased the expression levels of NF-kappa B-regulated genes, including genes involved in tumor cell proliferation (Cyclin D1, COX-2 and c-Myc), apoptosis (Survivin, Bcl-2, Bcl-xl, XIAP, IAP-1), invasion (MMP-9 and ICAM-1), and angiogenesis (VEGF). In athymic nu/nu mouse model, we further demonstrated that MA significantly suppressed pancreatic tumor growth, induced tumor apoptosis, and inhibited NF-kappa B-regulated anti-apoptotic gene expression, such as Survivin and Bcl-xl. ...data demonstrate that MA can potentiate the anti-tumor activities of TNFalpha and inhibit pancreatic tumor growth and invasion by activating caspase-dependent apoptotic pathway and by suppressing NF-kappa B activation and its downstream gene expression...

/ALTERNATIVE and IN VITRO TESTS/ Bioactivity-guided fractionation of apple peels was used to determine the chemical identity of bioactive constituents. Thirteen triterpenoids were isolated, and their chemical structures were identified. Antiproliferative activities of the triterpenoids against human HepG2 liver cancer cells, MCF-7 breast cancer cells, and Caco-2 colon cancer cells were evaluated. Most of the triterpenoids showed high potential anticancer activities against the three human cancer cell lines... All triterpenoids tested showed antiproliferative activity against Caco-2 cancer cells, especially 2alpha-hydroxyursolic acid, maslinic acid, 2alpha-hydroxy-3beta-{[(2E)-3-phenyl-1-oxo-2-propenyl]oxy}olean-12-en-28-oic acid, and 3beta-trans-p-coumaroyloxy-2alpha-hydroxyolean-12-en-28-oic acid, which displayed much higher antiproliferative activities...

For more Human Toxicity Excerpts (Complete) data for Maslinic Acid (8 total), please visit the HSDB record page.

Artificial Pollution SourcesMaslinic acid's production and use as a dietary supplement and as an ingredient in consumer products such as olive oil and skin care lotion products(1) may result in its release to the environment through various waste streams(SRC).
Environmental Bioconcentration · 1 Eintrag

An estimated BCF of 56 was calculated in fish for maslinic acid(SRC) using an estimated log Kow of 6.82(1) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is moderate(SRC).

Volatilization from Water/Soil · 1 Eintrag

The Henry's Law constant for maslinic acid is estimated as 3.5X10-11 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that maslinic acid is expected to be essentially nonvolatile from water surfaces(2). Maslinic acid's Henry's Law constant indicates that volatilization from moist soil surfaces is not expected to occur(SRC). Maslinic acid is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 2.3X10-15 mm Hg(SRC) determined from a fragment constant method(1).

Non-Human Toxicity Excerpts · 5 Einträge

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ The present study aimed to evaluate the protective effect of maslinic acid (MA) on body weight, heart weight, lipids, lipoproteins, lipid peroxidation (LPO), cardiac marker enzymes, and paraoxonase (PON) in normal control and isoproterenol (ISO)-induced myocardial infarcted albino Wistar rats. After treatment with MA (15 mg/kg) for 7 days, myocardial infarction was induced by subcutaneous injection of ISO (85 mg/kg) for two consecutive days. ISO caused a considerable decrease in body weight and increased the heart weight. The concentrations of total cholesterol, triglycerides, very low-density lipoprotein-cholesterol, and low-density lipoprotein-cholesterol were higher, whereas that of high-density lipoprotein-cholesterol was lower, in the serum of ISO-administered rats. The activities of the cardiac marker enzymes creatine kinase, alanine transaminase, aspartate transaminase, and gamma-glutamyl transferase and levels of malondialdehyde were elevated in the serum of ISO-treated rats. ISO-administered rats also exhibited a decline in the activity of PON. Pretreatment of rats with MA reduced the effects of ISO on all parameters tested... The observed cardioprotective effects may be due to the antihyperlipidemic potential of MA, inhibition of LPO, and antioxidant activity.

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ /This study/ examined the hypolipidemic effect of olive pomace extracts. Identification and quantitation of maslinic acid and oleanolic acid as the potentially effective components of the pomace extracts were carried out by high performance liquid chromatography methods. Hyperlipidemia was induced in male Sprague Dawley rats by feeding them with a high cholesterol diet for 30 days. The olive pomace extracts were supplemented (200 mg/kg body wt/day) for 15 days. The levels of serum total cholesterol, triglyceride, high density lipoprotein-cholesterol, low density lipoprotein-cholesterol, aspartate aminotransferase and alanine aminotransferase increased in rats with hyperlipidemia. Treatment with the olive pomace extracts significantly modulated the abnormalities induced by hyperlipidemia. Lipid accumulation was decreased in histological findings...

/LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ ... The purpose of this study was to evaluate whether high doses of maslinic acid have harmful effects on Swiss CD-1 male mice. The single oral administration of the pentacyclic triterpene at 1000 mg/kg to mice did not produce any signs of morbidity or mortality. The repeated daily oral administration of 50 mg/kg of maslinic acid for 28 days did not induce any sign of toxicity during the experimental period. Body weight did not differ between mice that received the triterpene and the control group. Similarly, hematological and biochemical variables were not affected by the treatment. Histopathologic examination of the organs revealed that there were no differences between the control and the treated mice. ...

/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ Maslinic acid (MA) is a pentacyclic triterpene used as a feed additive to stimulate growth, protein-turnover rates, and hyperplasia in fish. To further our understanding of cellular mechanisms underlying the action of MA, /the authors/ have used 2-DE coupled with MS to identify proteins differentially expressed in the livers of juvenile gilthead sea bream (Sparus aurata) grown under fish-farm conditions and fed with a 100 mg/kg MA-enriched diet (MA100) /for 210 days/. After the comparison of the protein profiles from MA100 fed fish and from control, 49 protein spots were found to be altered in abundance (> or = 2-fold). Analysis by MALDI-TOF/TOF allowed the unambiguous identification of 29 spots, corresponding to 19 different proteins. These proteins were: phosphoglucomutase, phosphoglucose isomerase, S-adenosyl methionine-dependent methyltransferase class I, aldehyde dehydrogenase, catalase, 6-phosphogluconate dehydrogenase, fumarylacetoacetate hydrolase, 4-hydroxyphenylpyruvic dioxygenase, methylmalonate-semialdehyde dehydrogenase, lysozyme, urate oxidase, elongation factor 2, 60 kDa heat-shock protein, 58 kDa glucose-regulated protein, cytokeratin E7, type-II keratin, intermediate filament proteins, 17-beta-hydroxysteroid dehydrogenase type 4, and kinase suppressor of Ras1. Western blot analysis of kinase suppressor of Ras1, glucose 6-phosphate dehydrogenase, elongation factor 2, 60 kDa heat-shock protein, and catalase supported the proteome evidence. ...

For more Non-Human Toxicity Excerpts (Complete) data for Maslinic Acid (17 total), please visit the HSDB record page.

Environmental Abiotic Degradation · 1 Eintrag

The rate constant for the vapor-phase reaction of maslinic acid with photochemically-produced hydroxyl radicals has been estimated as 1.3X10-10 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 3 hours at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). Maslinic acid is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(2). Maslinic acid contains a cyclic olefin and cyclic olefins can undergo sensitized photo-oxidation in surface waters exposed to sunlight via reaction with hydroxyl, singlet oxygen and RO2 radicals with half-lives on the order of 13 to 40 days at the water surface(3); therefore, photo-oxidation may be an important fate process for maslinic acid in natural water(SRC).

Probable Routes of Human Exposure · 1 Eintrag

Occupational exposure to maslinic acid may occur through dermal contact with this compound at workplaces where maslinic acid is produced or used. The general population is exposed to maslinic acid via ingestion of dietary supplements and foods containing maslinic acid, especially olive oil, and dermal contact with this compound in consumer products containing maslinic acid such skin care lotion products. (SRC)

Environmental Fate/Exposure Summary · 1 Eintrag

Maslinic acid's production and use as a dietary supplement and as an ingredient in consumer products such as olive oil and skin care lotion products may result in its release to the environment through various waste streams. Maslinic acid is found in a number of natural sources, most notably pomace olive oil, and other plants such as red dates, camellia, pomegranate and sage. If released to air, an estimated vapor pressure of 2.3X10-15 mm Hg at 25 °C indicates maslinic acid will exist solely in the particulate phase in the atmosphere. Particulate-phase maslinic acid will be removed from the atmosphere by wet and dry deposition. If released to soil, maslinic acid is expected to have low mobility based upon an estimated Koc of 1760. The pKa of maslinic acid is 4.81, indicating that this compound will exist partially in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 3.5X10-11 atm-cu m/mole. Maslinic acid is not expected to volatilize from dry soil surfaces based upon its vapor pressure. Biodegradation data in soil or water were not available. If released into water, maslinic acid is expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is not expected to be an important fate process based upon this compound's estimated Henry's Law constant. An estimated BCF of 56 suggests the potential for bioconcentration in aquatic organisms is moderate. Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions. Maslinic acid contains a cyclic olefin and cyclic olefins can undergo sensitized photo-oxidation in surface waters exposed to sunlight via reaction with hydroxyl, singlet oxygen and RO2 radicals with half-lives on the order of 13 to 40 days at the water surface. Occupational exposure to maslinic acid may occur through dermal contact with this compound at workplaces where maslinic acid is produced or used. The general population is exposed to maslinic acid via ingestion of dietary supplements and foods containing maslinic acid, especially olive oil, and dermal contact with this compound in consumer products containing maslinic acid such skin care lotion products. (SRC)

Sicherheitsdaten

wgk
3
hs_code
29181990
safety_code
24/25
Speicherklasse
13 - Non Combustible Solids
Giftige Stoffe Daten
4373-41-5(Hazardous Substances Data)

Chemie und Industrie

Pharmakologische Informationen

Mechanism of Action · 3 Einträge

Maslinic acid, a pentacyclic triterpene found in the protective wax-like coating of the leaves and fruit of Olea europaea L., is a promising agent for the prevention of colon cancer. Investigators have shown /previously/ that maslinic acid inhibits cell proliferation to a significant extent and activates mitochondrial apoptosis in colon cancer cells. /This study/ investigated... this compound's apoptotic molecular mechanism. /Investigators/ used HT29 adenocarcinoma cells. Changes /in/ genotoxicity were analyzed by single-cell gel electrophoresis (comet assay). The cell cycle was determined by flow cytometry. Finally, changes in protein expression were examined by western blotting. Student's t-test was used for statistical comparison. HT29 cells treated with maslinic acid showed significant increases in genotoxicity and cell-cycle arrest during the G0/G1 phase after 72 hours treatment and an apoptotic sub-G0/G1 peak after 96 hours... the anti-tumoral activity of maslinic acid might proceed via p53-mediated apoptosis by acting upon the main signaling components that lead to an increase in p53 activity and the induction of the rest of the factors that participate in the apoptotic pathway. /Investigators/ found that in HT29 cells maslinic acid activated the expression of c-Jun NH2-terminal kinase (JNK), thus inducing p53. Treatment of tumor cells with maslinic acid also resulted in an increase in the expression of Bid and Bax, repression of Bcl-2, release of cytochrome-c and an increase in the expression of caspases -9, -3, and -7. Moreover, maslinic acid produced belated caspase-8 activity, thus amplifying the initial mitochondrial apoptotic signaling. All these results suggest that maslinic acid induces apoptosis in human HT29 colon-cancer cells through the JNK-Bid-mediated mitochondrial apoptotic pathway via the activation of p53...

Maslinic acid (2-alpha, 3-beta-dihydroxyolean-12-en-28-oic acid) is a natural triterpenoid compound from Olea europaea. This compound prevents oxidative stress and pro-inflammatory cytokine generation in vitro. This study ...investigated the anti-inflammatory effects of maslinic acid in central nervous system by using rat astrocyte cultures stimulated with lipopolysaccharide (LPS). /It/ evaluated different proteins implicated in the nuclear factor kappa B (NF-kappa B) signal transducer pathway employing Western blot and quantitative real time PCR techniques. Results demonstrated that maslinic acid treatment exerted potent anti-inflammatory action by inhibiting the production of Nitric Oxide and tumor necrosis factor alpha (TNF-alpha). Western blot analysis showed that maslinic acid treatment attenuated LPS-induced translocation of NF-kappa B p65 subunit to the nucleus and prevented LPS-induced I kappa B alpha phosphorylation in a concentration-dependent manner, Moreover, maslinic acid significantly suppressed the expression of cyclooxygenase 2 (COX-2) and inducible nitric oxide synthase (iNOS) at protein and mRNA levels. These results suggest that maslinic acid can potentially reduce neuroinflammation by inhibiting NF-kappa B signal transducer pathway in cultured cortical astrocytes.

Activation of NF-kappaB and MAPK/activator protein 1 (AP-1) signaling pathways by receptor activator NF-kappaB ligand (RANKL) is essential for osteoclast activity. Targeting NF-kappaB and MAPK/AP-1 signaling to modulate osteoclast activity has been a promising strategy for osteoclast-related diseases. /This study/ examined the effects of maslinic acid (MA), a pentacyclic triterpene acid that is widely present in dietary plants, on RANKL-induced osteoclastogenesis, osteoclast function, and signaling pathways by in vitro and in vivo assay systems. In mouse bone marrow monocytes (BMMs) and RAW264.7 cells, MA inhibited RANKL-induced osteoclastogenesis in a dose-dependent manner within nongrowth inhibitory concentration, and MA decreased osteoclastogenesis-related marker gene expression, including TRACP, MMP9, c-Src, CTR, and cathepsin K. Specifically, MA suppressed osteoclastogenesis and actin ring formation at early stage. In ovariectomized mice, administration of MA prevented ovariectomy-induced bone loss by inhibiting osteoclast activity. At molecular levels, MA abrogated the phosphorylation of MAPKs and AP-1 activity, inhibited the Ikappa Balpha phosphorylation and degradation, blocked NF-kappaB/p65 phosphorylation, nuclear translocation, and DNA-binding activity by downregulating RANK expression and blocking RANK interaction with TRAF6. Together /this/ data demonstrate that MA suppresses RANKL-induced osteoclastogenesis through NF-kappa B and MAPK/AP-1 signaling pathways and that MA is a promising agent in the treatment of osteoclast-related diseases such as osteoporosis.

Cellular LocationsExtracellular

Verwendung und Herstellung

Uses · 5 Einträge

Maslinic acid is reported to have potent antioxidant, anti-cancer, anti-HIV and anti-inflammatory activities

Maslinic acid is a protease inhibitor that, among other features, has the capacity of regulating cell growth. It is useful for cancer treatment, as it allows to control the hyperplasia and hypertrophy processes, typical of this disease.

... investigated the mechanisms of maslinic acid with regard to its inhibitory effects on the growth of HT29 colon-cancer cells. High concentrations of maslinic acid are present in the protective wax-like coating of olives. Our results show that treatment with maslinic acid results in a significant inhibition of cell proliferation in a dose-dependent manner and causes apoptotic death in colon-cancer cells. We found that it inhibits considerably the expression of Bcl-2 whilst increasing that of Bax; it also stimulates the release of mitochondrial cytochrome-c and activates caspase-9 and caspase-3. All these results point clearly to the activation of the mitochondrial apoptotic pathway in response to the treatment of HT29 colon-cancer cells with maslinic acid. Our results suggest that maslinic acid has the potential to provide significant natural defence against colon-cancer.

Maslinic acid has multiple biological and antimicrobial activities including anti-malarial activity

For more Uses (Complete) data for Maslinic Acid (6 total), please visit the HSDB record page.

General Manufacturing Information · 2 Einträge

... Interest for maslinic acid has increased because of its beneficial effects on health, which include antitumoral, antidiabetic, and antioxidant activities. Moreover, it has been attributed to anti-HIV and antiparasitic effects as well as vasorelaxant and stimulant of growth and protein-turnover properties.

Malinic acid is available as a dietary supplement as being a strong antioxidant and natural anti-inflammatory; available in consumer products such as olive oil, high protein fiber bars and skin care lotion products

Anwendungen · 2 Einträge

BeschreibungMaslinic acid (2-α,3-β-dihydroxyolean-12-en-28-oic acid) is a pentacyclic triterpene abundant in the cuticular lipid layer of olive fruits (Bianchi et al.,1994) .It is a compound of 30 carbon atoms grouped in five cycles that have several substitutes. Maslinic acid presents two hydroxyl groups bound to carbons 2 and 3,one carboxyl group bound to carbon 17, and a double bond between carbons 12 and 13.It is a highly hydrophobic compound of low water solubility. Maslinic acid is synthesized in plants via the cytoplasmic acetate/mevalonate pathway that leads to oxidosqualene (Seo et al., 1988).Oxidosqualene is cycled by various oxidosqualene cyclases, among them β-amyrin synthase, which catalyzes the transformation of oxydosqualene into β-amyrin (olean-12-3n-3β-ol). Afterwards,β-amyrin is converted by successive reactions into erythrodiol, oleanolic acid, and finally maslinic acid (Saimaru et al.,2007; Stiti et al.,2007).

VerwendenMaslinic Acid is an apoptosis inducer in lung cancer cells, occuring under normoxic and hypoxic conditions.

Anbieter100 Anbieter

成都普瑞法科技开发有限公司+86-028-82633397 18982077548 · [email protected]
南京普怡生物科技有限公司13814510036 · [email protected]
成都埃法生物科技有限公司028-028-85142057 19983342022 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
成都市久鼎化学技术有限公司18584079237 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]
上海科骊科生物技术有限公司021-34975789 18721102763 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
南宁赛菲尔生物科技有限公司18877121284;15078879878 · [email protected]
上海晶抗生物工程有限公司021-54721350 13524668266 · [email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
武汉卡诺斯科技有限公司027-83238443 15327105076 · [email protected]
上海诗丹德标准技术服务有限公司021-021-57127007-6622-6622 17621252073 · [email protected]
成都普思生物科技股份有限公司028-85370565-229 18080489829 · [email protected]
成都普菲德生物技术有限公司028-82610909 13388174823 · [email protected]
上海融禾医药科技发展有限公司17301719108 13341702378 · [email protected]
上海泰坦科技股份有限公司4006009262 13023226327 · [email protected]
上海隆盛化工有限公司58099637 13585536065 · [email protected]
MedChemexpress LLC021-58955995 · [email protected]
Zhejiang J&C Biological Technology Co.,Limited+1-2135480471 · [email protected]
长沙上禾生物科技有限公司0731-84213302 18975842720 · [email protected]
潍坊华植生物科技有限公司17388075642 13815430202 · [email protected]
南京春秋生物工程有限公司17388075642 13815430202 · [email protected]
Aktin Chemicals, Inc.028-85159085 · [email protected]
云南西力生物技术股份有限公司0871-65217109 · [email protected]
四川库利南科技有限公司400-1166-196 18981987031 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]
成都锦然生物科技有限公司028-83311324 1278112614 · [email protected]
成都瑞芬思德丹生物科技有限公司2355253622; 18981954830 · [email protected]
上海倍卓生物科技有限公司021-61119791,13386096464 · [email protected]
东晟凯瑞(上海)医药科技有限公司15800326364 18051538752 · [email protected]
HBCChem, Inc.+1-510-219-6317 · [email protected]
上海笛柏生物科技有限公司400-008-9730,021-54359730 400-008-9730 · [email protected]
Labnetwork lnc.+86-27-50766799 +86-18062016861 · [email protected]
雷丁试剂0510-85629785 18013409632 · [email protected]
上海卓因生物科技有限公司021-61317773 · [email protected]
上海麦克林生化科技股份有限公司15221275939 15221275939 · [email protected]
上海永叶生物科技有限公司86-021-61559134 15921386130 · [email protected]
南京百鑫德诺生物科技有限公司025-58849295 · [email protected]
池州凯隆进出口贸易有限公司[email protected]
Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
AN PharmaTech Co Ltd86(21)68097365 · [email protected]
TargetMol中国(陶术生物)021-021-33632979 15002134094 · [email protected]
武汉天植生物技术有限公司18607101326 15172504745 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
上海皓之翔生物科技有限公司(原上海拓青化工有限公司)526763801 13301653310 · [email protected]
Wuhan ChemNorm Biotech Co.,Ltd.+86-27-8439 4403 18971486879 · [email protected]
厦门志信化学有限公司+86-5922680277 +86-13806087780 · [email protected]
Alfa Chemistry+1-5166625404 · [email protected]
EMMX Biotechnology LLC888-539-0666 · [email protected]
Ergänzende Hinweise · 1 Eintrag

DefinitionMaslinic acid is a pentacyclic triterpenoid that is olean-12-ene substituted by hydroxy groups at positions 2 and 3 and a carboxy group at position 28 (the 2alpha,3beta stereoisomer). It is isolated from Olea europaea and Salvia canariensis and exhibits anti-inflammatory, antioxidant and antineoplastic activity. It has a role as an antioxidant, an antineoplastic agent, an anti-inflammatory agent and a plant metabolite. It is a pentacyclic triterpenoid and a dihydroxy monocarboxylic acid. It derives from a hydride of an oleanane.

Zugehörige Reaktionen

0
Reaktionsaufzeichnung erstellen

Keine Reaktionsaufzeichnungen unter den aktuellen Filterkriterien.

Notizen zur Verbindung

Wird geladen…

Auf dieser SeiteGrundinformationenÜberblickNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung