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Details

Stereochemistry ABSOLUTE
Molecular Formula C30H48O3
Molecular Weight 456.7003
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OLEANOLIC ACID

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

InChI

InChIKey=MIJYXULNPSFWEK-GTOFXWBISA-N
InChI=1S/C30H48O3/c1-25(2)14-16-30(24(32)33)17-15-28(6)19(20(30)18-25)8-9-22-27(5)12-11-23(31)26(3,4)21(27)10-13-29(22,28)7/h8,20-23,31H,9-18H2,1-7H3,(H,32,33)/t20-,21-,22+,23-,27-,28+,29+,30-/m0/s1

HIDE SMILES / InChI

Molecular Formula C30H48O3
Molecular Weight 456.7003
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 8 / 8
E/Z Centers 0
Optical Activity UNSPECIFIED

Sodium Oleanolate is a natural active ingredient derived from many plants. This pentacyclic triterpenoid acid is manufactured by extraction of Salvia officinalis leaves, also known as common sage, Loquat leaves and Olea europea. It can be also found mainly in the balm of rosemary leaves. Ursolic acid and Oleanolic acid have an isomer structure and belong to one of the strongest triterpenoids, which is of most interest to use in Anti-Aging and Anti-Photo-Aging products.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Inactive ingredient
PREVENTAGE FIRMING DEFENSE NORMAL/OILY BROAD SPECTRUM SPF 15 MERLE NORMAN

Approved Use

Unknown
Inactive ingredient
24 HOUR PIMPLE PUNISHER

Approved Use

For treatment of Acne. Helps keep skin clear of new acne blemishes.
Preventing
Unknown

Approved Use

Unknown
Secondary
Unknown

Approved Use

Unknown
Secondary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Anti-AIDS agents 38. Anti-HIV activity of 3-O-acyl ursolic acid derivatives.
2000 Dec
Two new triterpenoid saponins from Aralia subcapitata.
2001
A new biologically active triterpenoid saponin from the leaves of Lepidagathis hyalina Nees.
2001
A new triterpenoidal saponin from Ixeris sonchifolia and its cytotoxic activity.
2001 Aug
Cloning and characterization of a cDNA encoding beta-amyrin synthase involved in glycyrrhizin and soyasaponin biosyntheses in licorice.
2001 Aug
Haplophytin-A and B: the alkaloidal constituents of Haplophyllum acutifolium.
2001 Aug
Screening of triterpenoids isolated from Phyllanthus flexuosus for DNA topoisomerase inhibitory activity.
2001 Dec
Junceosides A-C, new triterpene saponins from Arenaria juncea.
2001 Dec
The first naturally occurring Tie2 kinase inhibitor.
2001 Dec 13
Extraction, isolation and characterisation of antitumor principle, alpha-hederin, from the seeds of Nigella sativa.
2001 Feb
Determination of binding constant of transcription factor AP-1 and DNA. Application of inhibitors.
2001 Feb
Effect of six compounds isolated from rhizome of Anemone raddeana on the superoxide generation in human neutrophil.
2001 Jan 26
Inhibitory role of GDP on saikosaponin (I) stimulated enzymes secretion and rising of [Ca2+]i in rat pancreatic acini.
2001 Jul
Three new acylated triterpene saponins from Acanthophyllum squarrosum.
2001 Jul
Inhibition of prostaglandin E2 production by platycodin D isolated from the root of Platycodon grandiflorum.
2001 Jun
Effects of Quillaja saponins on growth, metabolism, egg production and muscle cholesterol in individually reared Nile tilapia (Oreochromis niloticus).
2001 Jun
In vitro antileishmanial activity of three saponins isolated from ivy, alpha-hederin, beta-hederin and hederacolchiside A(1), in association with pentamidine and amphotericin B.
2001 Jun
Pregnene derivatives from Solenostemma argel leaves.
2001 Jun
Kalopanaxsaponin A is a basic saponin structure for the anti-tumor activity of hederagenin monodesmosides.
2001 Mar
Endothelin-1 has a unique oxygen-saving effect by increasing contractile efficiency in the isolated rat heart.
2001 Mar 20
Ursene type nortriterpene from Debregeasia salicifolia.
2001 May
A synthetic triterpenoid selectively inhibits the induction of matrix metalloproteinases 1 and 13 by inflammatory cytokines.
2001 May
[In vitro study of the antimutagenic activity of alphahederin].
2001 May-Jun
Hepatoprotective action of an oleanolic acid-enriched extract of Ligustrum lucidum fruits is mediated through an enhancement on hepatic glutathione regeneration capacity in mice.
2001 Nov
Triterpenoids.
2001 Oct
Nitric oxide and tumor necrosis factor-alpha production by oleanolic acid via nuclear factor-kappaB activation in macrophages.
2001 Oct 19
Cancer chemopreventive agents, serratane-type triterpenoids from Picea jezoensis.
2001 Oct 30
Acetylated triterpene saponins from the Thai medicinal plant, Sapindus emarginatus.
2001 Sep
Protective effect of endothelin type A receptor antagonist on brain edema and injury after transient middle cerebral artery occlusion in rats.
2001 Sep
Development of C-20 modified betulinic acid derivatives as antitumor agents.
2001 Sep 3
Gastroprotective activity of oleanolic acid derivatives on experimentally induced gastric lesions in rats and mice.
2002 Apr
In vitro antiinflammatory activity of kalopanaxsaponin A isolated from Kalopanax pictus in murine macrophage RAW 264.7 cells.
2002 Apr
A new naphthoquinone from Polygonum aviculare.
2002 Apr
High performance liquid chromatography analysis of canthinone alkaloids from Eurycoma longifolia.
2002 Apr
HPLC analysis of plasma 9-methoxycanthin-6-one from Eurycoma longifolia and its application in a bioavailability/pharmacokinetic study.
2002 Apr
Three new triterpene saponins from two species of Carpolobia.
2002 Apr
Quantification of the group B soyasaponins by high-performance liquid chromatography.
2002 Apr 24
A novel dicyanotriterpenoid, 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-onitrile, active at picomolar concentrations for inhibition of nitric oxide production.
2002 Apr 8
Production of bioactive triterpenes by Eriobotrya japonica calli.
2002 Feb
Antinociceptive and anti-rheumatoidal effects of Kalopanax pictus extract and its saponin components in experimental animals.
2002 Feb
Phytosterol content in American ginseng seed oil.
2002 Feb 13
Toxin clues to beetle relationships.
2002 Feb 19
Saponins-mediated potentiation of cisplatin accumulation and cytotoxicity in human colon cancer cells.
2002 Jan
Inhibition of alpha-glucosidase by oleanolic acid and its synthetic derivatives.
2002 Jun
Induction of differentiation in rat C6 glioma cells with Saikosaponins.
2002 Mar
Microbial transformations of two lupane-type triterpenes and anti-tumor-promoting effects of the transformation products.
2002 Mar
Quantitative determination for cytotoxic Friedo-nor-oleanane derivatives from five morphological types of Maytenus ilicifolia (Celastraceae) by reverse-phase high-performance liquid chromatography.
2002 Mar-Apr
[Comparative study of cytotoxic and hemolytic effects of triterpenoids isolated from Ginseng and Sea cucumber].
2002 Mar-Apr
The novel triterpenoid 2-cyano-3,12-dioxooleana-1,9-dien-28-oic acid (CDDO) potently enhances apoptosis induced by tumor necrosis factor in human leukemia cells.
2002 May 10
RP-LC determination of oleane derivatives in Terminalia arjuna.
2002 May 15
Patents

Sample Use Guides

In model of kidney disease, oleanolic acid was dissolved in 2% w/v dimethyl sulfoxide (DMSO) and then diluted with distilled water for each injection to a final DMSO concentration of 0.2% w/v. Oleanolic acid or vehicle was administered intraperitoneally (60 mg/kg i.p). one day before UUO, and was continued for 3 or 7 days after surgery.
Route of Administration: Other
In Vitro Use Guide
For cell viability assay, HepG2 cells were plated at a density of 5000 per well in a 96-well plate. After culturing overnight, the cells were exposed to fresh medium containing different concentrations of OA. 24 hours later, the cell viability was determined by CellTiter-Glo Luminescence Cell Viability Assay (Promega) according to the manufacturer’s instructions. In order to determine whether OA would affect the activity of FXR-LBD, HepG2 cells were transfected with an expression vector for Gal4-DBD-FXR-LBD, a reporter plasmid pFR-Luc, an internal control Renilla luciferase vector and then treated with FXR agonist CDCA in the presence of increasing amounts of OA.
Substance Class Chemical
Created
by admin
on Thu Jul 06 02:07:24 UTC 2023
Edited
by admin
on Thu Jul 06 02:07:24 UTC 2023
Record UNII
6SMK8R7TGJ
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OLEANOLIC ACID
INCI   MI   WHO-DD  
INCI  
Official Name English
OLEANIC ACID
Common Name English
(3.BETA.)-3-HYDROXYOLEAN-12-EN-28-OIC ACID
Common Name English
OLEANOLIC ACID (CONSTITUENT OF HOLY BASIL LEAF) [DSC]
Common Name English
OLEANOLIC ACID (CONSTITUENT OF BANABA LEAF) [DSC]
Common Name English
ASTRANTIAGENIN C
Common Name English
GIGANTEUMGENIN C
Common Name English
VIRGAUREAGENIN B
Common Name English
Oleanolic acid [WHO-DD]
Common Name English
OLEANOLIC ACID [INCI]
Common Name English
OLEANOLIC ACID [MI]
Common Name English
OLEANOLIC ACID [USP-RS]
Common Name English
OLEONOLIC ACID
Common Name English
OLEANOLATE
Common Name English
3.BETA.-HYDROXYOLEAN-12-EN-28-OIC ACID
Common Name English
NSC-114945
Code English
OLEANOL
Common Name English
GLEDIGENIN 1
Common Name English
CARYOPHYLLIN
Common Name English
Classification Tree Code System Code
DSLD 1800 (Number of products:12)
Created by admin on Thu Jul 06 02:07:24 UTC 2023 , Edited by admin on Thu Jul 06 02:07:24 UTC 2023
Code System Code Type Description
CHEBI
82828
Created by admin on Thu Jul 06 02:07:24 UTC 2023 , Edited by admin on Thu Jul 06 02:07:24 UTC 2023
PRIMARY
CAS
508-02-1
Created by admin on Thu Jul 06 02:07:24 UTC 2023 , Edited by admin on Thu Jul 06 02:07:24 UTC 2023
PRIMARY
EVMPD
SUB33853
Created by admin on Thu Jul 06 02:07:24 UTC 2023 , Edited by admin on Thu Jul 06 02:07:24 UTC 2023
PRIMARY
WIKIPEDIA
OLEANOLIC ACID
Created by admin on Thu Jul 06 02:07:24 UTC 2023 , Edited by admin on Thu Jul 06 02:07:24 UTC 2023
PRIMARY
ECHA (EC/EINECS)
208-081-6
Created by admin on Thu Jul 06 02:07:24 UTC 2023 , Edited by admin on Thu Jul 06 02:07:24 UTC 2023
PRIMARY
RXCUI
1370638
Created by admin on Thu Jul 06 02:07:24 UTC 2023 , Edited by admin on Thu Jul 06 02:07:24 UTC 2023
ALTERNATIVE
FDA UNII
6SMK8R7TGJ
Created by admin on Thu Jul 06 02:07:24 UTC 2023 , Edited by admin on Thu Jul 06 02:07:24 UTC 2023
PRIMARY
MESH
D009828
Created by admin on Thu Jul 06 02:07:24 UTC 2023 , Edited by admin on Thu Jul 06 02:07:24 UTC 2023
PRIMARY
NSC
114945
Created by admin on Thu Jul 06 02:07:24 UTC 2023 , Edited by admin on Thu Jul 06 02:07:24 UTC 2023
PRIMARY
RXCUI
1426254
Created by admin on Thu Jul 06 02:07:24 UTC 2023 , Edited by admin on Thu Jul 06 02:07:24 UTC 2023
PRIMARY RxNorm
EPA CompTox
DTXSID50858790
Created by admin on Thu Jul 06 02:07:24 UTC 2023 , Edited by admin on Thu Jul 06 02:07:24 UTC 2023
PRIMARY
SMS_ID
100000127756
Created by admin on Thu Jul 06 02:07:24 UTC 2023 , Edited by admin on Thu Jul 06 02:07:24 UTC 2023
PRIMARY
RS_ITEM_NUM
1478141
Created by admin on Thu Jul 06 02:07:24 UTC 2023 , Edited by admin on Thu Jul 06 02:07:24 UTC 2023
PRIMARY
MERCK INDEX
M8190
Created by admin on Thu Jul 06 02:07:24 UTC 2023 , Edited by admin on Thu Jul 06 02:07:24 UTC 2023
PRIMARY Merck Index
CHEBI
37659
Created by admin on Thu Jul 06 02:07:24 UTC 2023 , Edited by admin on Thu Jul 06 02:07:24 UTC 2023
PRIMARY
DAILYMED
6SMK8R7TGJ
Created by admin on Thu Jul 06 02:07:24 UTC 2023 , Edited by admin on Thu Jul 06 02:07:24 UTC 2023
PRIMARY
PUBCHEM
10494
Created by admin on Thu Jul 06 02:07:24 UTC 2023 , Edited by admin on Thu Jul 06 02:07:24 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT
ASSAY (HPLC)
PARENT -> CONSTITUENT ALWAYS PRESENT
CALENDULA OFFICINALIS FLOWER terpenoid
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
USP
PARENT -> CONSTITUENT ALWAYS PRESENT
PARENT -> CONSTITUENT ALWAYS PRESENT
SALT/SOLVATE -> PARENT
PARENT -> CONSTITUENT ALWAYS PRESENT
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ACTIVE MOIETY