Oleanic acid

Iupac Name：(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

CAS No.：508-02-1

Molecular Weight：456.70032

Introduction: 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. View more+

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1. Names and Identifiers

1.1 Name: Oleanic acid
1.2 Synonyms: (3-beta)-3-hydroxyolean-12-en-28-oicacid (3-beta)-olean-12-en-28-oicaci (3beta)-olean-12-en-28-oicaci 3-beta-Hydroxyolean-12-en-28-oic acid 3-beta-hydroxy-olean-12-en-28-oicaci Araligenin astrantiageninc CARYOPHYLLIN EINECS 208-081-6 Gledigeni Guagenin MFCD00064914 MoMorgenin Olean-12-en-28-oicacid, 3-hydroxy-, (3β)- Oleanic acid，Oleanolic acid oleanoic acid Oleanol Oleanolic Oleanolic Acid Oleanolic acid Extract Oleanolic Acid Hydrate Oleanolicacid Taragenin Taraligenin

1.3 CAS No.: 508-02-1

1.4 CID: 10494

1.5 EINECS(EC#): 208-081-6

1.6 Molecular Formula: C30H48O3 (isomer)

1.7 Inchi: 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

1.8 InChkey: MIJYXULNPSFWEK-GTOFXWBISA-N

1.9 Canonical Smiles: CC1(CCC2(CCC3(C(=CCC4C3(CCC5C4(CCC(C5(C)C)O)C)C)C2C1)C)C(=O)O)C

1.10 Isomers Smiles: C[C@]12CC[C@@H](C([C@@H]1CC[C@@]3([C@@H]2CC=C4[C@]3(CC[C@@]5([C@H]4CC(CC5)(C)C)C(=O)O)C)C)(C)C)O

2. Properties

3.1 Density: 1.1

3.1 Melting point: >300℃

3.1 Boiling point: 553.5 °C at 760 mmHg

3.1 Refractive index: 1.557

3.1 Flash Point: 302.6 °C

3.1 Precise Quality: 456.36000

3.1 PSA: 57.53000

3.1 logP: 7.23360

3.1 Appearance: light yellow

3.2 Chemical Properties: White Solid

3.3 Color/Form: Powder

3.4 pKa: 2.52(at 25℃)

3.5 Water Solubility: Insoluble

3.6 Stability: Stable at normal temperatures and pressures.

3.7 StorageTemp: 2-8°C

3. Use and Manufacturing

4.1 Definition: ChEBI: A pentacyclic triterpenoid that is olean-12-en-28-oic acid substituted by a beta-hydroxy group at position 3. Oleanic acidSupplier

4.2 Storage: Keep Cold.

4.3 Usage: A triterpenoid known for its anti-inflammatory properties, is commonly present in several medicinal plants.

4. Safety and Handling

5.1 Hazard Codes: Xi

5.1 Risk Statements: R36/37/38

5.1 Safety Statements: S26;S36

5.1 RIDADR: NONH for all modes of transport

5.1 WGK Germany: 2

5.1 RTECS: RK0177965

5.1 Safety: Hazard Codes:?Xi
Risk Statements: 36/37/38?
R36/37/38: Oleanolic acid (CAS NO. 508-02-1) is irritating to eyes, respiratory system and skin.
Safety Statements: 26-36/37/39?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.
WGK Germany: 2
RTECS: RK0177965

5.2 Specification: ?Oleanolic acid (CAS NO.508-02-1) is a naturally occurring triterpenoid, which distributed in food and medicinal plants, related to betulinic acid. And it can be widely? found in Phytolacca americana (American pokeweed), and Syzygium spp, garlic, etc.?It is?quite non-toxic, antitumor, and hepatoprotective, as well as exhibiting antiviral properties.

5.3 Toxicity

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	1500mg/kg (1500mg/kg)	?	Journal of Pharmacy and Pharmacology. Vol. 44, Pg. 456, 1992.
mouse	LD50	oral	> 2gm/kg (2000mg/kg)	?	Journal of Pharmacy and Pharmacology. Vol. 44, Pg. 456, 1992.
rat	LD50	intraperitoneal	> 2gm/kg (2000mg/kg)	?	Drugs of the Future. Vol. 19, Pg. 450, 1994.
rat	LD50	oral	> 2gm/kg (2000mg/kg)	?	Journal of Pharmacy and Pharmacology. Vol. 44, Pg. 456, 1992.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s)	No symbol.
Signal word	No signal word.
Hazard statement(s)	none
Precautionary statement(s)
Prevention	none
Response	none
Storage	none
Disposal	none

2.3 Other hazards which do not result in classification

none

View all

6. NMR Spectrum

IR : KBr disc

IR : nujol mull

7. Synthesis Route

508-02-1Total: 90 Synthesis Route

77-52-1 512 Suppliers

508-02-1 304 Suppliers

915-32-2

1724-17-0 16 Suppliers

Literatures:
Tetrahedron Letters, , vol. 46, # 13 p. 2337 - 2340
Yield: ~21%

127-09-3 856 Suppliers

77-52-1 512 Suppliers

508-02-1 304 Suppliers

Literatures:
Journal of the Chemical Society, Chemical Communications, , # 14 p. 1141 - 1143
Yield: null

1724-17-0 16 Suppliers

508-02-1 304 Suppliers

Literatures:
Sengupta, Pasupati; Sen, Manju; Das, Saktipada Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1980 , vol. 19, # 8 p. 721 - 722
Yield: ~67%

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8. Precursor and Product

precursor:

86438-29-1

33783-82-3

62498-83-3

89827-13-4

14162-53-9

77-52-1

1724-17-0

6153-31-7

4339-72-4

58546-61-5

25493-69-0

19897-43-9

91204-06-7

127-09-3

26020-14-4

90138-26-4

View all

product :

892869-54-4

303114-51-4

892869-55-5

4373-41-5

110700-49-7

17990-42-0

471-67-0

130216-67-0

1679-02-3

218600-53-4

892869-52-2

486-34-0

113306-85-7

218600-50-1

582-16-1

488-23-3

View all

9. Other Information

9.0 Merck: 14,6827

9.1 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.

9.2 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

9.3 Chemical Properties: White Solid

9.4 Physical properties: Appearance: Olea europaea exists in white needle crystal with ethanol or methanol. Melting point: It melts at 306–310?°C. Solubility: The ingredient is insoluble in water. Specific optical rotation: Polarized light rotates +83.3° when it passes through chloroform with concentration of 6?mol/L.

9.5 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.

9.6 Uses: A triterpenoid known for its anti-inflammatory properties, is commonly present in several medicinal plants. Inhibits secretory phospholipase A2.

9.7 Uses: A triterpenoid known for its anti-inflammatory properties, is commonly present in several medicinal plants.

9.8 Indications: It 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.

9.9 Definition: ChEBI: A pentacyclic triterpenoid that is olean-12-en-28-oic acid substituted by a beta-hydroxy group at position 3.

9.10 General Description: Oleanolic acid is a hydroxyl pentacyclic triterpenoic acid (HPTA), which exhibits antibacterial, antitumor and antileishmanial activity.

10. Computational chemical data