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Oleanolic acid

CAS No.
508-02-1
Chemical Name:
Oleanolic acid
Synonyms
oleanic acid;Oleanolic;Oleanoic Acid;CARYOPHYLLIN;Oleanlic Acid;eanoL;Oleanol;Guagenin;Gledigeni;Taragenin
CBNumber:
CB9113460
Molecular Formula:
C30H48O3
Molecular Weight:
456.7
MDL Number:
MFCD00064914
MOL File:
508-02-1.mol
MSDS File:
SDS
Last updated:2024-12-24 09:07:39

Oleanolic acid Properties

Melting point >300 °C (lit.)
alpha D20 +83.3° (c = 0.6 in chloroform)
Boiling point 502.79°C (rough estimate)
Density 1.0261 (rough estimate)
refractive index 1.4940 (estimate)
storage temp. 2-8°C
solubility Chloroform (Very Slightly), DMSO (Slightly, Heated), Methanol (Slightly, Heated)
form Solid
pka 2.52(at 25℃)
color light yellow
optical activity +83.320 (c 0.6, CHCl3)
Merck 14,6827
InChIKey NZQIXFRGWXNLSP-IDYUENATSA-N
LogP 8.576 (est)
CAS DataBase Reference 508-02-1(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII 6SMK8R7TGJ
EPA Substance Registry System Oleanolic acid (508-02-1)

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictograms
GHS07
Signal word  Warning
Hazard statements  H315-H319-H335
Precautionary statements  P261-P280a-P304+P340-P305+P351+P338-P405-P501a
Hazard Codes  Xi
Risk Statements  36/37/38
Safety Statements  26-36-37/39-60-37
WGK Germany  2
RTECS  RK0177965
TSCA  Yes
HS Code  29181990
NFPA 704
1
2 0

Oleanolic acid price More Price(43)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 42515 Oleanolic acid analytical standard 508-02-1 10mg $183 2024-03-01 Buy
Sigma-Aldrich 1478141 Oleanolic acid United States Pharmacopeia (USP) Reference Standard 508-02-1 15MG $351 2022-05-15 Buy
TCI Chemical O0317 Oleanolic Acid Hydrate >98.0%(T) 508-02-1 5g $76 2024-03-01 Buy
TCI Chemical O0317 Oleanolic Acid Hydrate >98.0%(T) 508-02-1 25g $235 2024-03-01 Buy
Alfa Aesar H60445 Oleanolic acid, 97% 508-02-1 250mg $175 2024-03-01 Buy
Product number Packaging Price Buy
42515 10mg $183 Buy
1478141 15MG $351 Buy
O0317 5g $76 Buy
O0317 25g $235 Buy
H60445 250mg $175 Buy

Oleanolic acid Chemical Properties,Uses,Production

Description

Oleanolic 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.

Chemical Properties

White needle-like crystals (ethanol), odorless, tasteless. Unstable to acid and alkali. Insoluble in water, soluble in methanol, ethanol, ethyl ether, acetone and chloroform.

Occurrence

The 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.

History

The 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.

Uses

Oleanolic 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.?

Definition

ChEBI: 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.

Indications

Oleanolic acid is included in the Pharmacopoeia of the People's Republic of China (Part 2, volume 3), the British Pharmacopoeia (2017), and the European Pharmacopoeia (8.7th ed.). It is mainly used for the adjuvant treatment of acute infectious icteric hepatitis and acute and chronic hepatitis. It also can be utilized in psoriasis, rheumatoid arthritis, nephritic edema, ascites, stomach with turbid, metrorrhagia, bruises, carbuncle, soreness and weakness of the waist and knees, fetal irritability and so on.

General Description

Oleanolic 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.

Biochem/physiol Actions

Triterpenoid isolated from medicinal plants. Antitumor and hepatoprotective agent. Oleanolic acid has therapeutic potential for neurodegenerative diseases.

Pharmacology

Liver protection: Pretreatment of 100?mg/kg once a day for 3?days can protect the liver and decrease the activity of enzymes. It achieves by increasing the amount of metallothioneins and liver glucoside transferases to prevent glutathione emptying, to inhibit several subtypes of P450 oxidase, and to prevent combination with toxic substances.
Antimicrobial and antiviral effect: Oleanolic acid may inhibit the proliferation or production of NO induced by interferon or in the macrophages by competitively binding to the enzymes necessary for the growth and reproduction of microorganisms or virus and play an anti-inflammatory and antiviral role. EC50 of HIV-1- infected H9 cells is 3.4?mol/L.
Effects on metabolism of glucose and lipid: The treatment of 50–100?mg/kg for 4?days achieves the glucosidase activity inhibition, reduction of glucose absorption, inhibition of glycogen phosphorylase, activation of glycogen synthesis, inhibition of protein tyrosine phosphatase 1B, regulation of insulin signaling pathway, and increase of insulin sensitivity, and it may also be achieved by inhibiting the transport of glucose from the stomach to the intestine and transport activity of intestinal villi. 200?mg/kg suspension administrated by gavage for 4?weeks decreases the level of triglycerides, cholesterol, and β-lipoprotein in high-fat animal, and it contributes to increased platelet swimming rate and decreased blood viscosity
Effects on immunologic function: 60?mg/kg intraperitoneal injection may regulate the immune system by inhibiting type I allergic reaction, promoting proliferation of lymphocyte and inhibiting enzyme C-3? in the traditional complement pathway.
Antioxidant effect: It fights against lipid peroxidation by scavenging free radicals.
Other functions: 10–5?mol/L oleanolic acid may inhibit the activity of DNA ligase I active site. It exerts anticancer and anti-mutation effects, and IC50 value is2.2×105 ?mol/L in inhibiting ornithine decarboxylase (ODC) induced by external TPA at the transcriptional level. Oleanolic acid in polyvinylpyrrolidone suspension at the dose of 16?mg/kg by intragastric administration for 30?days also reversibly decreases quality and exercise capacity of mouse sperms.
It is reported that it is consistent with the single compartment model, or noncompartmental model, and may be distributed in the compound in accordance with the two compartment models. Eventually, it will be eliminated by P450 oxidase in the liver.

Clinical Use

It is reported that contrast with Western medicine, the 60~90?mg/d oleanolic acid tablets supplemented with vitamin B can treat acute and chronic hepatitis, with effective rates of 94.4% and 69.81%, respectively, in clinical results. It has been listed on the drug manual as adjuvant therapy for acute and chronic hepatitis.

References

1.https://en.wikipedia.org/wirki/Oleanolic_acid
2.https://www.ncbi.nlm.nih.gov/mesh/68009828
3.http://www.sciencedirect.com/science/article/pii/S0031942212000027
4.http://www.adooq.com/oleanolic-acid-caryophyllin.html

1458622-89-3
508-02-1
Synthesis of Oleanolic acid from Olean-12-en-28-oic acid, 3-[(O-β-D-xylopyranosyl-(1→3)-O-6-deoxy-α-L-mannopyranosyl-(1→2)-O-[β-D-glucopyranosyl-(1→4)]-α-L-arabinopyranosyl)oxy]-, O-6-deoxy-α-L-mannopyranosyl-(1→4)-O-β-D-glucopyranosyl-(1→6)-β-D-glucopyranosyl ester, (3β)-

Oleanolic acid Preparation Products And Raw materials

Global( 614)Suppliers
Supplier Tel Email Country ProdList Advantage
PNP Biotech Co. Ltd
+8618516098983 sales@pnpbiotech.com China 1001 58
Hovane Phytochemicals Co., Ltd
+86-17340288373 victor.liu@hovane.com China 32 58
Hebei Weibang Biotechnology Co., Ltd
+8615531157085 abby@weibangbio.com China 8807 58
Hebei Yanxi Chemical Co., Ltd.
+8617531190177 peter@yan-xi.com China 5857 58
Hebei Chuanghai Biotechnology Co,.LTD
+86-13131129325 sales1@chuanghaibio.com China 5889 58
Hebei Weibang Biotechnology Co., Ltd
+8617732866630 bess@weibangbio.com China 18151 58
Hebei Kingfiner Technology Development Co.Ltd
+86-15532196582 +86-15373005021 lisa@kingfinertech.com China 3009 58
Shaanxi Haibo Biotechnology Co., Ltd
+undefined18602966907 qinhe02@xaltbio.com China 997 58
Hebei Zhuanglai Chemical Trading Co.,Ltd
+8613343047651 admin@zlchemi.com China 3002 58
Hebei Shengyang Water Conservancy Engineering Co., Ltd.
+8615373025980 clara@hbshengyang.com China 875 58

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Oleanolic Acid pictures 2024-12-25 Oleanolic Acid
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US $10.00 / kg 1kg 98% Titration 10000 Changsha Staherb Natural Ingredients Co., Ltd.
Oleanic acid; Ligustrum lucidum Ext pictures 2024-12-25 Oleanic acid; Ligustrum lucidum Ext
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US $0.00-0.00 / kg 1kg 98% HPLC 1000kg Changsha Staherb Natural Ingredients Co., Ltd.
Oleanolic Acid pictures 2024-12-25 Oleanolic Acid
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US $0.00-0.00 / kg 1kg 98%HPLC 1 ton Hovane Phytochemicals Co., Ltd
  • Oleanolic Acid pictures
  • Oleanolic Acid
    508-02-1
  • US $10.00 / kg
  • 98% Titration
  • Changsha Staherb Natural Ingredients Co., Ltd.
  • Oleanolic Acid pictures
  • Oleanolic Acid
    508-02-1
  • US $0.00-0.00 / kg
  • 98%HPLC
  • Hovane Phytochemicals Co., Ltd
(3-beta)-3-hydroxyolean-12-en-28-oicacid (3-beta)-olean-12-en-28-oicaci (3beta)-olean-12-en-28-oicaci 3-beta-hydroxy-olean-12-en-28-oicaci astrantiageninc Oleanolic acid Extract Olean-12-en-28-oicacid, 3-hydroxy-, (3β)- Oleanic acid,Oleanolic acid 3β-Hydroxy-20-methyl-29-norurs-12-ene-28-oic acid OLEANOLIC ACID METHYL ESTER(SH) Olealic acid CARYOPHYLLIN(DISCONTINUED) See 15302-25(SH) Oleanolic Acid (Caryophyllin) Araligenin Gledigeni Guagenin Gledigenin 1 NSC 114945 Oleanolic Acid  giganteumgeninc virgaureageninb CARYOPHYLLIN hplc OLEANOLIC ACID WITH HPLC OLEANOLIC ACID, NATURAL OLAQUINDOCIS 3-HYDROXYOLEAN-12-EN-28-OIC ACID 3BETA-HYDROXYOLEAN-12-EN-28-OIC ACID 3B-HYDROXYOLEAN-12-EN-28-OIC ACID OLEANOLIC ACID OLEANOLIC ACID HYDRATE oieanolic acid OLEANDIC ACID Oleanol CARYOPHYLLIN(SH) OLEANOLIC ACID(P) OLEANOLIC ACID(RG) OLEANOLIC ACID(SH) (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 Oleanolic acid dihydrate, froM HeMsleya chinensis Astrantigeninc Caryophyllia (4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-hydroxy-2,2,6a,6b,9,9,12a-heptaMethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid Oleanolic acid >=97% Oleanolic Acid Hydrate, 98.0%(T) Oleanolic acid, >=98% Mistletoe sapogenin MoMorgenin Panaxsapogenin Sugarbeet acid Swertiaic acid Taragenin Taraligenin Oleanolic acid 508-02-1 Oleanic acid price qidunguos 12.(3-BETA)-3-HYDROXYOLEAN-12-EN-28-OIC ACID Oleanolic Acid P.E. Oleanolic acid dihydrate, 98%, from Hemsleya chinensis