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Oleanolic Acid

HCID 10494
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Basic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

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
Molecular formula
C30H48O3
Average molar mass
456.7 g/mol
Monoisotopic mass
456.36034539

Names & identifiers

Preferred 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
English name
Oleanolic acid
Molecular formula
C30H48O3
Molecular weight
456.7

Names & synonyms

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
Show more names
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

Database identifiers

CAS
508-02-1
PubChem CID
10494
DTXSID
DTXSID50858790
ChEMBL
CHEMBL168
ChEBI
CHEBI:37659
UNII
6SMK8R7TGJ
EC Number
208-081-6
Nikkaji
J6.235I

Properties

Computed structural propertiesFilling in

XLogP
7.5
Topological polar surface area
57.5 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
3
Rotatable bonds
1
Heavy atoms
33
Formal charge
0
Complexity
885

Experimental & physicochemical properties

Melting Point310 °C
Physical DescriptionSolid

Physicochemical properties

Melting point
300 °C · >300 °C (lit.)
Boiling point
502.79 °C · 502.79°C (rough estimate)
alpha
20 · D20 +83.3° (c = 0.6 in chloroform)
Density
1.0261 · 1.0261 (rough estimate)
refractive index
1.494 · 1.4940 (estimate)
storage temp.
2 · 2-8°C
solubility
Chloroform (Very Slightly), DMSO (Slightly, Heated), Methanol (Slightly, Heated)
form
Solid
pka
2.52 · 2.52(at 25℃)
color
light yellow
optical activity
83.32 · +83.320 (c 0.6, CHCl3)

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 3 items

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.

Hazard information

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

Regulatory information

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

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
2
tsca
TSCA listed
rtecs
RK0177965
hs_code

Chemistry & industry

Pharmacology

Cellular LocationsExtracellular;Membrane

Uses & manufacturing

General Manufacturing InformationOlean-12-en-28-oic acid, 3-hydroxy-, (3.beta.)-: ACTIVE
Applications · 5 items

DescriptionOleanolic 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.

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Related reactions

3 records
New reaction record
HRID 580310 reaction equation
HRID 580310As reactantuspto-grants-1988_06
HRID 2190248 reaction equation
HRID 2190248As reactantuspto-grants-2012_12
HRID 2190252 reaction equation
HRID 2190252As reactantuspto-grants-2012_12

Compound notes

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On this pageBasic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
Merck
14 · 14,6827
Cosmetics Ingredients Functions
SKIN CONDITIONING
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 DataBase Reference
508 · 508-02-1(CAS DataBase Reference)
EWG's Food Scores
1 · 1
FDA UNII
6 SMK8R7TGJ · 6SMK8R7TGJ
EPA Substance Registry System
Oleanolic acid (508-02-1)
UNSPSC Code
85151701 · 85151701
NACRES
24 · NA.24
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
315 · H315-H319-H335
Precautionary statements
261 · P261-P280a-P304+P340-P305+P351+P338-P405-P501a
PPE
95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes
Xi
Risk Statements
36 · 36/37/38
Safety Statements
26 · 26-36-37/39-60-37
WGK Germany
2 · 2
RTECS
177965 · RK0177965
TSCA
TSCA listed
HS Code
29181990 · 29181990
Storage Class
11 · 11 - Combustible Solids
29181990
risk_code
36/37/38
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xi
safety_code
26-36-37/39-60-37
Storage Class
11 - Combustible Solids
Hazard statements
H315-H319-H335
Precautionary statements
P261-P280a-P304+P340-P305+P351+P338-P405-P501a

UsesOleanolic 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.

General DescriptionOleanolic acid is a hydroxyl pentacyclic triterpenoic acid (HPTA), which exhibits antibacterial, antitumor and antileishmanial activity. It is biosynthesized from lupane. It can rearrange to the isomer, ursolic acid, or be oxidized to taraxasterol and amyrin.

Upstream & downstream products

Downstream products

Bardoxolone methylEthyl (3beta)-3-hydroxyolean-12-en-28-oate3-Oxo-olean-12-en-28-oic acidBardoxoloneOleanolic acid benzoate
Additional notes · 1 item

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.