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3β-Hydroxyolean-12-en-28-sure

Oleanolic Acid

HCID 10494
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GrundinformationenNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
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Grundinformationen

CAS
508-02-1
Standard-SMILES
CC1(C)CC[C@]2(C(=O)O)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CC[C@H](O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]2C1
InChIKey
MIJYXULNPSFWEK-GTOFXWBISA-N
Summenformel
C30H48O3
Durchschnittliche Molmasse
456,7 g/mol
Monoisotopische Masse
456,36034539

Namen und Bezeichner

Bevorzugter Name
Oleanolic Acid
IUPAC
(4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-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
Lokaler Name
3β-Hydroxyolean-12-en-28-sure
Englischer Name
Oleanolic acid
Summenformel
C30H48O3
Molmasse
456.7

Namen und Synonyme

OLEANOLIC ACID508-02-1Oleanic acidCaryophyllinAstrantiagenin CGiganteumgenin CVirgaureagenin B3beta-Hydroxyolean-12-en-28-oic acidOleanololeonolic acid(4aS,6aR,6aS,6bR,8aR,10S,12aR,14bS)-10-hydroxy-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 acid6SMK8R7TGJ
Weitere Namen anzeigen
OleanolicOleanoic AcidOleanlic AcidOLEANOLIC ACID HYDRATE(3-beta)-olean-12-en-28-oicaci3-HYDROXYOLEAN-12-EN-28-OIC ACID(3-beta)-3-hydroxyolean-12-en-28-oicacideanoL
NSC-114945Olean-12-en-28-oic acid, 3-hydroxy-, (3beta)-DTXSID50858790CHEBI:37659Triterpenes, OleananeRefChem:6084DTXCID701474453208-081-6

Datenbank-Bezeichner

Eigenschaften

Berechnete Struktureigenschaften

XLogP
7,5
Polarare Oberfläche (TPSA)
57,5 Ų
H-Brücken-Donoren
2
H-Brücken-Akzeptoren
3
Frei drehbare Bindungen
1
Schwere Atome
33
Formalladung
0
Komplexität
885

Experimentelle und physikochemische Eigenschaften

Melting Point310 °C
Physical DescriptionSolid

Physikochemische Eigenschaften

Schmelzpunkt
300 °C · >300 °C (lit.)
Siedepunkt
502.79 °C · 502.79°C (rough estimate)
Dichte
1.0261 · 1.0261 (rough estimate)
Brechungsindex
1.494 · 1.4940 (estimate)
storage temp.
2 · 2-8°C
Löslichkeit
Chloroform (Very Slightly), DMSO (Slightly, Heated), Methanol (Slightly, Heated)
Aggregatzustand
Solid
pka
2.52 · 2.52(at 25℃)
Farbe
light yellow
Merck
14 · 14,6827
Kosmetik-Inhaltsstoffe Funktionen
SKIN CONDITIONING

Sicherheit und Regulatorisches

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

GHS-Klassifizierung

GHS Classification · 3 Einträge

This chemical does not meet GHS hazard criteria for 94.4% (68 of 72) of all reports.

Not Classified;Reported as not meeting GHS hazard criteria by 68 of 72 companies (only 5.6% companies provided GHS information). For more detailed information, please visit ECHA C&L website.

Aggregated GHS information provided per 72 reports by companies from 5 notifications to the ECHA C&L Inventory.;Reported as not meeting GHS hazard criteria per 68 of 72 reports by companies.;There are 3 notifications provided by 4 of 72 reports by companies with hazard statement code(s).;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Gefahrenhinweise

Regulatory InformationChemical: Olean-12-en-28-oic acid, 3-hydroxy-, (3.beta.)-
Hazard Classes and CategoriesNot Classified

Regulatorische Informationen

Regulatory InformationChemical: Olean-12-en-28-oic acid, 3-hydroxy-, (3.beta.)-

Sicherheitsdaten

wgk
2
tsca
TSCA listed
hs_code
29181990
RTECS-Nr.
RK0177965

Chemie und Industrie

Pharmakologische Informationen

Cellular LocationsExtracellular;Membrane

Verwendung und Herstellung

General Manufacturing InformationOlean-12-en-28-oic acid, 3-hydroxy-, (3.beta.)-: ACTIVE
Anwendungen · 4 Einträge

BeschreibungOleanolic acid or oleanic acid is a naturally occurring pentacyclic triterpenoid with the formula of C30H48O3. It was found in the non-glyceride fraction of olive pomace oil and is widely distributed in food and plants where it exists as a free acid or as an aglycone precursor for triterpenoid saponins, in which it can be linked to one or more sugar chains. It is biosynthesized from lupane. It can rearrange to the isomer, ursolic acid, or be oxidized to taraxasterol and amyrin. Oleanolic acid and its derivatives possess several promising pharmacological activities, such as hepatoprotective effects, and anti-inflammatory, antioxidant, or anticancer activities.

OccurrenceThe ingredient is mainly extracted from the leaves of Olea europaea and Viscum album L. Besides, it is found in the fruit of ligustrum lucidum ait, the whole grass of swertia mileensis t.n.he et w.l.shi, s. mussotii franch, the leaves and roots of astrantia major, the root bark and stem bark of aralia chinensis, the roots of hemsleya macrosperma c.y.wu , the roots of hemsleya amabilis diels, and the roots of hemsleya chinensis cogn. There is a long history in the herb and fruit which contain oleanolic acid. They play an important role in the treatment of various diseases. Oleanolic acid may be the most effective component in various Chinese medicines.

HistoryThe chemical formula was first identified in 1918. In 1960, Khastgir purified the compound for the first time. Corey identified the structure of oleanolic acid in 1993.Now the compound has been made into a drug and is being marketed in China. As early as 2002, the tablet form of oleanolic acid was listed. In 2010, capsule preparations came into the market, and to date, there is no other listed preparation. Sanofi treated it as antiulcer and NSAIDs candidate in abroad.Although it has anti-inflammatory and anti-ulcer effects, Sanofi stopped the study of developing oleanolic acid into a drug in 1989.

Zugehörige Reaktionen

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Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 580310
HRID 580310als Eduktuspto-grants-1988_06
Reaktionsgleichung von HRID 2190248
HRID 2190248als Eduktuspto-grants-2012_12
Reaktionsgleichung von HRID 2190252
HRID 2190252als Eduktuspto-grants-2012_12

Notizen zur Verbindung

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Auf dieser SeiteGrundinformationenNamen und BezeichnerEigenschaftenSicherheit und RegulatorischesChemie und IndustrieZugehörige ReaktionenNotizen zur Verbindung
CAS
508-02-1
PubChem CID
10494
DTXSID
DTXSID50858790
ChEMBL
CHEMBL168
ChEBI
CHEBI:37659
UNII
6SMK8R7TGJ
EC Number
208-081-6
Nikkaji
J6.235I
InChIKey
NZQIXFRGWXNLSP-IDYUENATSA-N
SMILES
[H][C@@]12CC(C)(C)CC[C@@]1(CC[C@]3(C)C2=CC[C@]4([H])[C@@]5(C)CC[C@H](O)C(C)(C)[C@]5([H])CC[C@@]34C)C(O)=O
LogP
8.576 · 8.576 (est)
CAS Datenbank
508 · 508-02-1(CAS DataBase Reference)
EPA chemische Informationen
Oleanolic acid (508-02-1)
risk_code
36/37/38
hazard_code
Xi
safety_code
26-36-37/39-60-37
Speicherklasse
11 - Combustible Solids

VerwendenOleanolic acid is a triterpenoid known for its anti-inflammatory properties, is commonly present in several medicinal plants. It can Inhibits secretory phospholipase A2 that is mainly used for the treatment of acute jaundiced hepatitis with remarkable efficacy, and also has good effect on chronic hepatitis.

Vor- und nachgelagerte Produkte

Nachgelagerte Produkte

Bardoxolone methylEthyl (3beta)-3-hydroxyolean-12-en-28-oate3-Oxo-olean-12-en-28-oic acidBardoxoloneOleanolic acid benzoate

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Ergänzende Hinweise · 1 Eintrag

DefinitionChEBI: Oleanolic acid is a pentacyclic triterpenoid that is olean-12-en-28-oic acid substituted by a beta-hydroxy group at position 3. It has a role as a plant metabolite. It is a pentacyclic triterpenoid and a hydroxy monocarboxylic acid. It is a conjugate acid of an oleanolate. It derives from a hydride of an oleanane.