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Details

Stereochemistry ABSOLUTE
Molecular Formula C30H48O3
Molecular Weight 456.7014
Optical Activity UNSPECIFIED
Defined Stereocenters 8 / 8
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OLEANOLIC ACID

SMILES

CC1(C)CC[C@@]2(CC[C@]3(C)C(=CC[C@]4([H])[C@@]5(C)CC[C@@]([H])(C(C)(C)[C@]5([H])CC[C@]43C)O)[C@]2([H])C1)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 456.7014
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
Two new triterpenoid saponins from Aralia subcapitata.
2001
A new biologically active triterpenoid saponin from the leaves of Lepidagathis hyalina Nees.
2001
Saikosaponin v-1 from roots of Bupleurum chinense DC.
2001
Altered immunomodulating and toxicological properties of degraded Quillaja saponaria Molina saponins.
2001 Apr
Screening of triterpenoids isolated from Phyllanthus flexuosus for DNA topoisomerase inhibitory activity.
2001 Dec
Phytochemical and antimicrobial studies on Drynaria quercifolia.
2001 Dec
The first naturally occurring Tie2 kinase inhibitor.
2001 Dec 13
Synthesis and anti-HIV activity of oleanolic acid derivatives.
2001 Dec 17
Extraction, isolation and characterisation of antitumor principle, alpha-hederin, from the seeds of Nigella sativa.
2001 Feb
NMR and LC-MSn characterisation of two minor saponins from Ilex paraguariensis.
2001 Jan-Feb
Inhibitory role of GDP on saikosaponin (I) stimulated enzymes secretion and rising of [Ca2+]i in rat pancreatic acini.
2001 Jul
Purification of saponin compounds in Bupleurum falcatum by solvent partitioning and preparative LC.
2001 Jul
Effects of ginsenosides from Panax ginseng on cell-to-cell communication function mediated by gap junctions.
2001 Jul
Involvement of p-15(INK4b) and p-16(INK4a) gene expression in saikosaponin a and TPA-induced growth inhibition of HepG2 cells.
2001 Jul 13
Enantioselective synthesis and complement inhibitory assay of A/B-ring partial analogues of oleanolic acid.
2001 Jul 9
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
Inhibitory effects of triterpenoids and sterols on human immunodeficiency virus-1 reverse transcriptase.
2001 May
Ursene type nortriterpene from Debregeasia salicifolia.
2001 May
Studies on the constituents of Clematis species. VIII. Triterpenoid saponins from the aerial part of Clematis tibetana KUNTZ.
2001 May
Four new oleanane saponins from Anemone anhuiensis.
2001 May
D:A friedo-oleanane lactones from the stems of Mallotus repandus.
2001 May
Detoxification of lantana hepatotoxin, lantadene A, using Alcaligenes faecalis.
2001 May-Jun
[In vitro study of the antimutagenic activity of alphahederin].
2001 May-Jun
Efficient production of saikosaponins in Bupleurum falcatum root fragments combined with signal transducers.
2001 Nov
Antimycobacterial plant terpenoids.
2001 Nov
Two triterpene saponins from Achyranthes bidentata.
2001 Nov
Triterpenoids.
2001 Oct
Anti-AIDS agents. 48.(1) Anti-HIV activity of moronic acid derivatives and the new melliferone-related triterpenoid isolated from Brazilian propolis.
2001 Oct
Medicinal foodstuffs. XXVII. Saponin constituents of gotu kola (2): structures of new ursane- and oleanane-type triterpene oligoglycosides, centellasaponins B, C, and D, from Centella asiatica cultivated in Sri Lanka.
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
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
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
Phytosterol content in American ginseng seed oil.
2002 Feb 13
Spasmolytic effects of baccharis conferta and some of its constituents.
2002 Jan
Kalopanaxsaponin A from Kalopanax pictus, a potent antioxidant in the rheumatoidal rat treated with Freund's complete adjuvant reagent.
2002 Jan
Selective cytotoxicity of betulinic acid on tumor cell lines, but not on normal cells.
2002 Jan 10
Inhibition of alpha-glucosidase by oleanolic acid and its synthetic derivatives.
2002 Jun
The anti-inflammatory triterpenoid methyl 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oate methanol solvate hydrate.
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
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 Sat Jun 26 08:12:12 UTC 2021
Edited
by admin
on Sat Jun 26 08:12:12 UTC 2021
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
OLEANOLIC ACID [WHO-DD]
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 [INCI]
Common Name English
OLEANOLIC ACID [MI]
Common Name English
OLEANOLIC ACID [USP-RS]
Common Name English
OLEONOLIC ACID
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 Sat Jun 26 08:12:12 UTC 2021 , Edited by admin on Sat Jun 26 08:12:12 UTC 2021
Code System Code Type Description
USP_CATALOG
1478141
Created by admin on Sat Jun 26 08:12:12 UTC 2021 , Edited by admin on Sat Jun 26 08:12:12 UTC 2021
PRIMARY USP-RS
CAS
508-02-1
Created by admin on Sat Jun 26 08:12:12 UTC 2021 , Edited by admin on Sat Jun 26 08:12:12 UTC 2021
PRIMARY
EVMPD
SUB33853
Created by admin on Sat Jun 26 08:12:12 UTC 2021 , Edited by admin on Sat Jun 26 08:12:12 UTC 2021
PRIMARY
WIKIPEDIA
OLEANOLIC ACID
Created by admin on Sat Jun 26 08:12:12 UTC 2021 , Edited by admin on Sat Jun 26 08:12:12 UTC 2021
PRIMARY
ECHA (EC/EINECS)
208-081-6
Created by admin on Sat Jun 26 08:12:12 UTC 2021 , Edited by admin on Sat Jun 26 08:12:12 UTC 2021
PRIMARY
RXCUI
1370638
Created by admin on Sat Jun 26 08:12:12 UTC 2021 , Edited by admin on Sat Jun 26 08:12:12 UTC 2021
PRIMARY
FDA UNII
6SMK8R7TGJ
Created by admin on Sat Jun 26 08:12:12 UTC 2021 , Edited by admin on Sat Jun 26 08:12:12 UTC 2021
PRIMARY
MESH
D009828
Created by admin on Sat Jun 26 08:12:12 UTC 2021 , Edited by admin on Sat Jun 26 08:12:12 UTC 2021
PRIMARY
RXCUI
1426254
Created by admin on Sat Jun 26 08:12:12 UTC 2021 , Edited by admin on Sat Jun 26 08:12:12 UTC 2021
PRIMARY RxNorm
EPA CompTox
508-02-1
Created by admin on Sat Jun 26 08:12:12 UTC 2021 , Edited by admin on Sat Jun 26 08:12:12 UTC 2021
PRIMARY
MERCK INDEX
M8190
Created by admin on Sat Jun 26 08:12:12 UTC 2021 , Edited by admin on Sat Jun 26 08:12:12 UTC 2021
PRIMARY Merck Index
PUBCHEM
10494
Created by admin on Sat Jun 26 08:12:12 UTC 2021 , Edited by admin on Sat Jun 26 08:12:12 UTC 2021
PRIMARY
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