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Oleanic acid structure
Oleanic acid structure

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+
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:?IrritantXi
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.

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

6. NMR Spectrum
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
  • Molecular Weight:456.70032g/mol
  • Molecular Formula:C30H48O3
  • Compound Is Canonicalized:True
  • XLogP3-AA:7.5
  • Exact Mass:456.36034539
  • Monoisotopic Mass:456.36034539
  • Complexity:885
  • Rotatable Bond Count:1
  • Hydrogen Bond Donor Count:2
  • Hydrogen Bond Acceptor Count:3
  • Topological Polar Surface Area:57.5
  • Heavy Atom Count:33
  • Defined Atom Stereocenter Count:8
  • Undefined Atom Stereocenter Count:0
  • Defined Bond Stereocenter Count:0
  • Undefined Bond Stereocenter Count:0
  • Isotope Atom Count:0
  • Covalently-Bonded Unit Count:1
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