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HCID 5281233Erstellt: 27. Oktober 2026

Bis(6-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-8,8'-diapo-.psi.,.psi.-carotindioat

GARDENIN · Crocins · Crocin A · Crocin 1 · saffron(natural) · CROCETIN DIGENTIOBIOSYL ESTER · CROCIN · CrocinⅠ

https://huagongshe.com/de/chemical/5281233

Molekülstruktur von Bis(6-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-8,8'-diapo-.psi.,.psi.-carotindioat

Identifikatoren & physikalische Daten

CAS No.39465-00-4
SummenformelC44H64O24
Durchschnittliche Molmasse977 g/mol
Monoisotopische Masse976,37875293 g/mol
SMILESCC(/C=C/C=C(\C)C(=O)O[C@@H]1O[C@H](CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@H](O)[C@H]1O)=C\C=C\C=C(C)\C=C\C=C(/C)C(=O)O[C@@H]1O[C@H](CO[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)[C@@H](O)[C@H](O)[C@H]1O
InChIKeySEBIKDIMAPSUBY-RTJKDTQDSA-N
PubChem CID5281233
ChEMBLCHEMBL446785
ChEBICHEBI:79068
EC No.254-465-1
DTXSIDDTXSID7046172
Lokaler NameBis(6-O-β-D-glucopyranosyl-β-D-glucopyranosyl)-8,8'-diapo-.psi.,.psi.-carotindioat

Chemische & physikalische Eigenschaften

XLogP-2,5
Polarare Oberfläche (TPSA)391
H-Brücken-Donoren14
H-Brücken-Akzeptoren24
Frei drehbare Bindungen20
Schwere Atome68
Formalladung0
Komplexität1.730
LipideLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C40 isoprenoids (tetraterpenes) [PR0107]
Color/FormSolid /Di-gentiobiose ester/Hydrated brownish-red needles from methanol /Di-gentiobiose ester/
LöslichkeitFreely soluble in hot water, giving an orange-colored solution /Di-gentiobiose ester/Sparingly soluble in absolute alcohol, ether, other organic solvents /Di-gentiobiose ester/DMSO (Slightly, Heated), Methanol (Very Slightly, Sonicated)
Schmelzpunkt186 °C (effervescence) /Di-gentiobiose ester/186° (effervescence)
Physical DescriptionSolid
Stability/Shelf LifeThe kinetics of crocin and picrocrocin in whole and ground samples of saffron stored at different temperatures and relative humidities were studied. First-order kinetics were observed for crocin and second-order for picrocrocin. There was no deterioration of the samples stored at -17 °C or at 0 °C, the ideal storage conditions. A reduction in the relative humidity had a greater effect on stability than a decrease in temperature. Conditions that favor stability for picrocrocin also favor the stability of its aroma.Stable under recommended storage conditions.
Siedepunkt1169.0±65.0 °C(Predicted)
Dichte1.54±0.1 g/cm3(Predicted)
Lagerbedingungen2-8°C
AggregatzustandPowder
pKa (Säurekonstante)12.20±0.70(Predicted)
FarbeOrange to Very Dark Purple
Merck14,2589
StabilitätLight Sensitive
Hauptanwendungendiagnostic assay manufacturinghematologyhistology
Kosmetik-Inhaltsstoffe FunktionenANTIOXIDANTCOLORANT
InChIKeyOXNHRKGZZFWUQZ-QORFUXSJSA-N
LogP (Verteilungskoeffizient)-4.742 (est)
CAS Datenbank42553-65-1

Sicherheit & Vorschriften

GHS-EinstufungNot Classified
Regulatorische InformationenChemical: .beta.-D-Glucopyranose, 6-O-.beta.-D-glucopyranosyl-, 1,1'-[(2E,4E,6E,8E,10E,12E,14E)-2,6,11,15-tetramethyl-2,4,6,8,10,12,14-hexadecaheptaenedioate]
Special ReportsAlavizadeh SH, Hosseinzadeh HBioactivity assessment and toxicity of crocin: A comprehensive review. Food and Chemical Toxicology 64: 65-80 (2014)[Alavizadeh SH, Hosseinzadeh HFood and Chemical Toxicology 64: 65-80 (2014) http://www.clearsightclearmind.com/files/Alavizadeh_2014.pdf]
Hazard Classes and CategoriesNot Classified
Hazardous Reactivities and IncompatibilitiesIncompatible materials: Strong oxidizing agents.
Firefighting HazardsSpecial hazards arising from the substance or mixture: Carbon oxides.
BrandbekämpfungsverfahrenUse water spray, alcohol-resistant foam, dry chemical or carbon dioxide.Advice for firefighters: Wear self contained breathing apparatus for fire fighting if necessary.
LagerbedingungenConditions for safe storage, including any incompatibilities: Keep container tightly closed in a dry and well-ventilated place. Recommended storage temperature: 2 - 8 °C. Air and moisture sensitive. Light sensitive. Store under inert gas.
ReinigungsverfahrenAccidental Release Measures. Personal precautions, protective equipment and emergency procedures: Avoid dust formation. Avoid breathing vapours, mist or gas. Environmental precautions: Do not let product enter drains. Methods and materials for containment and cleaning up: Sweep up and shovel. Keep in suitable, closed containers for disposal.
EntsorgungsverfahrenSRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality

Anwendungen & Verwendung

Beschreibung

Crocin/Gardenia Extract is a Gardenia extract that contains crocin I, II, and III, and crocetin, among other compounds.

Verwenden

Crocin, is a natural carotenoid derived the flowers crocus and gardenia. Crocin has been shown to be a potent antioxidant. It has also been shown to have an antiproliferative action against cancer cells in vitro, and also possessing possible antidepressant properties.

potential migration in soil or water
effects on animal and plant life
and conformance with environmental and public health regulations.
Waste treatment methods. Product: Offer surplus and non-recyclable solutions to a licensed disposal company. Contaminated packaging: Dispose of as unused product.
Preventive MeasuresPrecautions for safe handling: Provide appropriate exhaust ventilation at places where dust is formed.Appropriate engineering controls: General industrial hygiene practice.Gloves must be inspected prior to use. Use proper glove removal technique (without touching glove's outer surface) to avoid skin contact with this product. Dispose of contaminated gloves after use in accordance with applicable laws and good laboratory practices. Wash and dry hands.SRP: Local exhaust ventilation should be applied wherever there is an incidence of point source emissions or dispersion of regulated contaminants in the work area. Ventilation control of the contaminant as close to its point of generation is both the most economical and safest method to minimize personnel exposure to airborne contaminants. Ensure that the local ventilation moves the contaminant away from the worker.
Personal Protective Equipment (PPE)Eye/face protection: Use equipment for eye protection tested and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).Skin protection: Handle with gloves.Body Protection: Choose body protection in relation to its type, to the concentration and amount of dangerous substances, and to the specific work-place., The type of protective equipment must be selected according to the concentration and amount of the dangerous substance at the specific workplace.Respiratory protection: Respiratory protection is not required. Where protection from nuisance levels of dusts are desired, use type N95 (US) or type P1 (EN 143) dust masks. Use respirators and components tested and approved under appropriate government standards such as NIOSH (US) or CEN (EU).
WechselwirkungenViper envenomation results in inflammation at the bitten site as well as target organs. Neutrophils and other polymorphonuclear leukocytes execute inflammation resolving mechanism and will undergo apoptosis after completing the task. However, the target specific toxins induce neutrophil apoptosis at the bitten site and in circulation prior to their function, thus reducing their number. Circulating activated neutrophils are major source of inflammatory cytokines and leakage of reactive oxygen species (ROS)/other toxic intermediates resulting in aggravation of inflammatory response at the bitten/target site. Therefore, neutralization of venom induced neutrophil apoptosis reduces inflammation besides increasing the functional neutrophil population. Therefore, the present study investigates the venom induced perturbances in isolated human neutrophils and its neutralization by crocin (Crocus sativus) a potent antioxidant carotenoid. Human neutrophils on treatment with venom resulted in altered ROS generation, intracellular Ca2+ mobilization, mitochondrial membrane depolarization, cyt-c translocation, caspase activation, phosphatidylserine externalization and DNA damage. On the other hand significant protection against oxidative stress and apoptosis were evidenced in crocin pre-treated groups. In conclusion the viper venom induces neutrophil apoptosis and results in aggravation of inflammation and tissue damage. The present study demands the necessity of an auxiliary therapy in addition to antivenin therapy to treat secondary/overlooked complications of envenomation.This study investigated the protective efficacy of crocin against hepatotoxicity induced by cyclophosphamide (CP) in Wistar rats. The experimental rats were treated with crocin orally at a dose of 10 mg/kg for 6 consecutive days after the administration of a single intraperitoneal dose of CP (150 mg/kg). The ameliorative effect of crocin on organ toxicity was studied by evaluating oxidative stress enzymes, inflammatory cytokines and histological sections. A single intraperitoneal CP injection significantly elevated endogenous reactive oxygen species and oxidation of lipids and proteins, which are the hallmarks of oxidative damage in liver and serum. In consequence, the primary defensive reduced glutathione, total thiol and antioxidant enzymes such as superoxide dismutase, catalase, glutathione-S-transferase and glutathione peroxidase, were significantly reduced. In addition, liver and serum aspartate aminotransferase and alanine aminotransferase along with acid and alkaline phosphatase were considerably increased. Oral administration of crocin significantly rejuvenated all the above altered markers to almost normal state. The protective efficacy of crocin was further supported by the histological assessment and restoration of CP-induced inflammatory cytokines and enzyme levels compared with the control drug. The results obtained suggest the protective nature of crocin against CP-induced oxidative damage/inflammation and organ toxicity.Acrylamide (ACR) is a potent neurotoxic in human and animal models. In this study, the effect of crocin, main constituent of Crocus sativus L. (Saffron) on ACR-induced cytotoxicity was evaluated using PC12 cells as a suitable in vitro model. The exposure of PC12 cells to ACR reduced cell viability, increased DNA fragmented cells and phosphatidylserine exposure, and elevated Bax/Bcl-2 ratio. Results showed that ACR increased intracellular reactive oxygen species (ROS) in cells and ROS played an important role in ACR cytotoxicity. The pretreatment of cells with 10-50 uM crocin before ACR treatment significantly attenuated ACR cytotoxicity in a dose-dependent manner. Crocin inhibited the downregulation of Bcl-2 and the upregulation of Bax and decreased apoptosis in treated cells. Also, crocin inhibited ROS generation in cells exposed to ACR. In conclusion, our results indicated that pretreatment with crocin protected cells from ACR-induced apoptosis partly by inhibition of intracellular ROS production.Crocus sativus L. has been shown to interact with the opioid system. Thus, the effects of aqueous and ethanolic extracts of stigma and its constituents were evaluated on morphine-withdrawal syndrome in mice. Dependence was induced using subcutaneous (s.c.) injections of morphine for 3 days. On day 4, morphine was injected 0.5 hr prior the intraperitoneal (i.p.) injections of the extracts, crocin, safranal, clonidine (0.3 mg/kg) or normal saline. Naloxone was injected (5 mg/kg i.p.) 2 hr after the final dose of morphine and the number of episodes of jumping during 30 min was considered as the intensity of the withdrawal syndrome. Clonidine, the aqueous and ethanolic extracts of saffron reduced the jumping activity. Safranal was injected (s.c.) 30 min prior and 1 and 2 hr after the injection of morphine. It potentiated some signs of withdrawal syndrome. The aqueous extract decreased the movement in all of the doses (80, 160, 320 mg/kg) and the ethanolic extract decreased it in the dose of 800 mg/kg in open field test. But crocin and the dose of 400 mg/kg ethanolic extract showed no effect on activity in this test. It is concluded that the extracts and crocin may have interaction with the opioid system to reduce withdrawal syndrome.For more Interactions (Complete) data for Crocin (13 total), please visit the HSDB record page.
ToxizitätsübersichtIDENTIFICATION AND USE: Crocin is a carotenoid constituent of saffron. It is used as a laboratory reagent, antioxidant and experimental antidote in snake bites and food dye. HUMAN EXPOSURE AND TOXICITY: Volunteers received 20 mg crocin tablets or placebo for one month. General measures of health were recorded during the study such as hematological, biochemical, hormonal and urinary parameters in pre and post-treatment periods. No major adverse events were reported during the trial. Crocin tablets did not change the above parameters except that it decreased amylase, mixed white blood cells and PTT in healthy volunteers after one month. Crocus sativus extract and its major constituent, crocin, significantly inhibited the growth of human colorectal cancer cells while not affecting normal cells. ANIMAL STUDIES: The acute and sub-acute toxicity of crocin was evaluated in mice: at pharmacological doses, crocin did not exhibit marked damages to any organs. With high doses (3 g/kg, IP or orally) after 24 and 48 hr no mortality was seen by crocin in mice. Developmental study suggests that crocin or safranal can induce embryonic malformations when administered in pregnant mice. Minor skeletal malformations were the most commonly observed abnormality. Behavioral studies in male rats revealed an aphrodisiac activity of saffron aqueous extract and its constituent crocin. Crocin gave negative results in bacterial test for mutagenicity (including the Ames test) and DNA damageit did not produce chromosome damage in mammalian cells in culture.
Plant ConcentrationsCrocin occurrences in plants(1).[Table#8195]
Natural Pollution SourcesCrocin is a highly unsaturated diterpene dicarboxylic acid found in saffron(1). /Di-gentiobiose ester/One of the yellow-red pigments of saffron /Di-gentiobiose ester/
Human Toxicity Excerpts/HUMAN EXPOSURE STUDIES/ Objective(s): Crocin is the chemical ingredient primarily responsible for the color of saffron. It has different pharmacological effects such as antioxidant, anticancer and memory improving activities. Crocin tablets were evaluated for short-term safety and tolerability in healthy adult volunteers. Materials and Methods: The study was a randomized, double-blind, placebo-controlled design consisting of one month treatment of crocin tablets. Volunteers who fulfilled inclusion and exclusion criteria were randomized into 2 groups of 22 each (males and females) and received 20 mg crocin tablets or placebo. General measures of health were recorded during the study such as hematological, biochemical, hormonal and urinary parameters in pre and post-treatment periods. Results: No major adverse events were reported during the trial. Crocin tablets did not change the above parameters except that it decreased amylase, mixed white blood cells and PTT in healthy volunteers after one month. Conclusion: This clinical safety evaluation showed a relatively safe and normal profile for crocin in healthy volunteers at the given doses within the trial period/ALTERNATIVE and IN VITRO TESTS/ /The aim of this study was/ to investigate the anti-proliferative effects of Crocus sativus extract and its major constituent, crocin, on three colorectal cancer cell lines (HCT-116, SW-480, and HT-29). The cell growth inhibition effect was compared to that of non-small cell lung cancer (NSCLC) cells. In addition, Crocus sativus' effect on non-cancer cells was evaluated. METHODS: Using high performance liquid chromatography (HPLC), the purity of crocin and the content of crocin extract were determined. Anti-proliferative effects of Crocus sativus extract and crocin on test cells was evaluated by MTS assay. The purity of crocin was found to be 95.9% and the content of crocin in the extract was 22.9%. Significant concentration-related inhibition effects of the extract on all three colorectal cancer cell lines were observed (P<0.01). The proliferation was reduced most significantly in HCT-116 cells, to 45.5% at 1.0 mg/mL and to 6.8% at 3.0 mg/mL. Crocin at 1.0 mM, significantly reduced HCT-116, SW-480, and HT-29 cell proliferation to 2.8%, 52%, and 16.8%, respectively (P<0.01). Since 3.0 mg/mL Crocus sativus extract contained approximately 0.6 mM crocin, the observed effects suggest that crocin is a major responsible constituent in the extract. Significant anti-proliferative effects were also observed in non-small cell lung cancer cells. However, Crocus sativus extract did not significantly affect the growth of non-cancer young adult mouse colon cells. Data from this study demonstrated that Crocus sativus extract and its major constituent, crocin, significantly inhibited the growth of colorectal cancer cells while not affecting normal cells. Crocus sativus extract should be investigated further as a viable option in the treatment of colorectal cancer./ALTERNATIVE and IN VITRO TESTS/ /The objective of this study was/ to investigate the changes of gene expression profile in transitional cell carcinoma of bladder T24 cell after crocin treatment, in order to find the possible crocin targets. The bladder cancer T24 cell line was treated with crocin. MTT assay was adopted to determine the inhibition rate for selecting the best effect time and concentration of crocin. Differentially expressed genes on groups with or without treatment of crocin were screened with high throughout cDNA microarray. One up-regulated gene p21(WAF1) and one down-regulated gene cyclinD1 were selected to undergo analysis by the reverse transcription polymerase chain reaction (RT-PCR). Moreover, immunocytochemical method was used to evaluate p21(WAF1) and cyclinD1 protein expression. The growth of T24 cells was inhibited remarkably following a marked positive correlation between crocin concentration, time and inhibitor rate. When 3 mmol x L(-1) crocin treated T24 cells for 48hr, the difference was significant compared with the control group (P < 0.05). Crocin induced wide changes of the gene expression profile of T24 cells. A total of 836 genes were up-regulated or down-regulated by more than 2 times, which were involved cell cycle controlling, DNA cell apoptosis, replication factor, and so on. The mRNA expression of p21(WAF1) and cyclinD1 detected by RT-PCR were in accordance with cDNA microarray data. The results of immunocytochemical method showed that p21(WAF1) and cyclin D1 protein expression were consistent with those mRNA expression. Crocin can induce the significant alteration of the gene expression profile of T24 cells. It is suggested that the widely konwn anti-tumor effects of crocin are medicated at least in part by regulating the cell cycle controlling gene expression./ALTERNATIVE and IN VITRO TESTS/ In this study, the mechanism of crocin action was investigated in the /human/ gastric adenocarcinoma (AGS) cells in comparison with human normal fibroblast skin cells (HFSF-PI3). Crocin revealed a dose- and time-dependent cytotoxic effect against an AGS cell line, as determined by 3-(4,5-Dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide assay. Crocin-induced apoptosis was evidenced by flow cytometry and measuring caspase activity. The increased sub-G1 population and activated caspases in the treated AGS cells confirmed its anticancer effect. Expression of both Bax and Bcl-2 was determined using a semiquantitative reverse transcriptase-polymerase chain reaction and Western blot in these cells before and after treatment with crocin. Apoptosis was significantly stimulated as indicated by increasing the Bax/Bcl-2 ratio after crocin treatment. All of the above-mentioned parameters remained normal in HFSF-PI3 treated with crocin. These data are providing insight into the molecular mechanisms underlying the crocin-induced apoptosis in the AGS cells, rendering it as the potential anticancer agent.For more Human Toxicity Excerpts (Complete) data for Crocin (8 total), please visit the HSDB record page.
Non-Human Toxicity Excerpts/LABORATORY ANIMALS: Acute Exposure/ The acute and sub-acute toxicity of crocin was evaluated in mice... At pharmacological doses, crocin did not exhibit marked damages to all major organs of the body. With high doses (3 g/kg, IP or orally) after 24 and 48 hr no mortality was seen by crocin in mice./LABORATORY ANIMALS: Acute Exposure/ Toxicity by subcutaneous injection was tested in mice and at 0.05 g./10 g. body weight, all remained alive, at 0.1 g./10 g., 3 out of 5 died, while at 0.15 g./10 g. all animals died. The duration of life, at above lethal dose, was 22 minutes in one case, 45-95 minutes in 3 cases, and 5 hours and 48 minutes in one case./LABORATORY ANIMALS: Acute Exposure/ By subcutaneous injection of crocin solution in mouse of 14-17 g. body weight, at around lethal dosage, respiration becomes somewhat fast after 10 minutes or so, the movement generally becomes sluggish, and the mouse stays crouched, not walking spontaneous. The animal moves if given external stimulation but the manner of walking is not normal, the hind legs being extended outside and the walking is clumsy. When the symptom is allowed to develop, the eyes are closed and respiration becomes faster, although the animal does move sluggishly if made to walk. At this stage, the animal will return to the normal abdominal position when placed on its back. As death approaches, respiration becomes fast and the animal jumps from time to time, but respiration stops and death results. Autopsy immediately after ceasure of respiration showed that the heart has stopped in a diastolic state. Generally speaking, subcutaneous injection results in death within 24 hours. When the dosage used is below lethal dose and the animal has escaped death, the sluggishness of the movement and loss of spontaneous movement are observed but the animal recovers gradually and there is hardly any perceptible change after 24 hours./LABORATORY ANIMALS: Acute Exposure/ Administration of crocin or crocetin sodium /to rabbits/ results in the increase of bile secretion for 1 hour or more after injection.For more Non-Human Toxicity Excerpts (Complete) data for Crocin (14 total), please visit the HSDB record page.
Antidote and Emergency Treatment/SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B//SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B//SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W TKO /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's (LR) if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/
F1-8-10
Wassergefährdungsklasse (WGK)3
Zollcode32129000
RTECS-Nr.HL7380000
Sicherheitshinweise (S)24/25
Lagerklasse11 - Combustible Solids
Gefahrstoffdaten42553-65-1(Hazardous Substances Data)