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Oleanolic acid information


Oleanolic acid[1]
Oleanolic acid
Names
IUPAC name
3β-Hydroxyolean-12-en-28-oic acid
Systematic IUPAC name
(4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-Hydroxy-2,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2H)-carboxylic acid
Other names
Oleanic acid
Identifiers
CAS Number
  • 508-02-1 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:37659 ☒N
ChEMBL
  • ChEMBL168 checkY
ChemSpider
  • 10062 checkY
ECHA InfoCard 100.007.347 Edit this at Wikidata
EC Number
  • 208-081-6
IUPHAR/BPS
  • 3306
PubChem CID
  • 10494
UNII
  • 6SMK8R7TGJ checkY
CompTox Dashboard (EPA)
  • DTXSID50858790 Edit this at Wikidata
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 checkY
    Key: MIJYXULNPSFWEK-GTOFXWBISA-N checkY
  • 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
    Key: MIJYXULNPSFWEK-GTOFXWBIBS
  • Key: MIJYXULNPSFWEK-GTOFXWBISA-N
SMILES
  • O=C(O)[C@@]54[C@H](/C3=C/C[C@H]1[C@](CC[C@@H]2[C@]1(C)CC[C@H](O)C2(C)C)(C)[C@]3(C)CC4)CC(C)(C)CC5
Properties
Chemical formula
C30H48O3
Molar mass 456.711 g·mol−1
Appearance White
Melting point > 300 °C (572 °F; 573 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)
Infobox references

Oleanolic acid or oleanic acid is a naturally occurring pentacyclic triterpenoid related to betulinic acid. It is widely distributed in food and plants where it exists as a free acid or as an aglycone of triterpenoid saponins.[2]

  1. ^ "Oleanolic acid". Sigma-Aldrich. Merck. Retrieved November 29, 2018.
  2. ^ Pollier J, Goossens A (May 2012). "Oleanolic acid". Phytochemistry. 77: 10–15. doi:10.1016/j.phytochem.2011.12.022. PMID 22377690.

and 27 Related for: Oleanolic acid information

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Oleanolic acid

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Oleanolic acid or oleanic acid is a naturally occurring pentacyclic triterpenoid related to betulinic acid. It is widely distributed in food and plants...

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List of phytochemicals in food

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maize, alfalfa. Oleanolic acid American pokeweed, honey mesquite, garlic, java apple, cloves, and many other Syzygium species. Ursolic acid apples, basil...

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Ursolic acid

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derivatives, such as experimental antitumor agents. Betulinic acid Moronic acid Oleanolic acid CID 64945 from PubChem Constituents of Mirabilis jalapa. Siddiqui...

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Limonene

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as the (R)-enantiomer, but racemizes at 300 °C. When warmed with mineral acid, limonene isomerizes to the conjugated diene α-terpinene (which can also...

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Hederagenin

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framework: Betulinic acid Boswellic acid Glycyrrhetinic acid Moronic acid Oleanolic acid Ursolic acid Corosolic acid Amyrin Lupeol Maslinic acid Hopane BIOPESTICIDES...

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Saponin

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particular note among these are sugar acids such as glucuronic acid and galacturonic acid, which are oxidized forms of glucose and galactose. Cardenolide...

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Triterpene

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PMID 19742422. Liu, Jie (December 1995). "Pharmacology of oleanolic acid and ursolic acid". Journal of Ethnopharmacology. 49 (2): 57–68. doi:10...

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Centella asiatica

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other known telomerase activators: oleanolic acid 5.9-fold, Astragalus extract 4.3-fold, TA-65 2.2-fold, and maslinic acid 2-fold. In the context of phytoremediation...

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Achyranthes aspera

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)" Achyranthes aspera contains triterpenoid saponins which possess oleanolic acid as the aglycone. Ecdysterone, an insect moulting hormone, and long chain...

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Ixora coccinea

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indicate that the plant contains the phytochemicals lupeol, ursolic acid, oleanolic acid, sitosterol, rutin, lecocyanadin, anthocyanins, proanthocyanidins...

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Tanghulu

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and chlorogenic acid, caffeic acid, maslinic acid, oleanolic acid, quercetin, ursolic acid, chrysin, epicatechin and other organic acids and nutritional...

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Prunella vulgaris

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betulinic acid, D-camphor, D-fenchone, cyanidin, delphinidin, hyperoside, manganese, lauric acid, oleanolic acid, rosmarinic acid, myristic acid, rutin,...

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Clove

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eugenin, kaempferol, rhamnetin, and eugenitin, triterpenoids such as oleanolic acid, stigmasterol, and campesterol and several sesquiterpenes. Although...

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Stellaria media

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The plant also contains triterpenoid saponins of the hydroxylated oleanolic acid type. Proanthocyanidins are present in the testa of seeds. Nanakusa-no-sekku...

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Terpenoid

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Triterpenes 6 30 C30H48 Amyrin, betulinic acid, limonoids, oleanolic acid, sterols, squalene, ursolic acid Tetraterpenoids Tetraterpenes 8 40 C40H64 Carotenoids...

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Nardostachys

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plant contains: acaciin ursolic acid octacosanol kanshone A nardosinonediol nardosinone aristolen-9beta-ol oleanolic acid beta-sitosterol Nardostachys jatamansi...

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Paracetamol

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hydrolysis with hydrochloric acid, 4-aminophenol reacts in ammonia solution with a phenol derivate, e.g. salicylic acid, to form an indophenol dye under...

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Mirabilis jalapa

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extract of the aerial parts yields β-sitosterol, stigmasterol, ursolic acid, oleanolic acid and brassicasterol. Bioassay-guided fractionation of an organic extract...

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Lycopene

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is similar, as are the enzymes involved. Synthesis begins with mevalonic acid, which is converted into dimethylallyl pyrophosphate. This is then condensed...

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Phytochemical

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categories, such as carotenoids and polyphenols, which include phenolic acids, flavonoids, stilbenes or lignans. Flavonoids can be further divided into...

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Terpene

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resist polymerization (low ceiling temperatures) but are susceptible to acid-induced carbocation formation. Selected terpenes Limonene, a monoterpene...

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Betel

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etc.), lignan (pinoresinol) and other components. Some of them are oleanolic acid, dehydropipernonaline, piperolein-B, bornyl cis-4-hydroxycinnamate and...

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Betalain

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betanin, the simplest betacyan. In addition, betalamic acid reacts spontaneously with various amino acids or amines to form yellow-orange colored betaxanthins...

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Amyrin

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biosynthesis, α-amyrin is the precursor of ursolic acid and β-amyrin is the precursor of oleanolic acid. All three amyrins occur in the surface wax of tomato...

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Capsaicin

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the branched-chain fatty acid pathway. To produce capsaicin, 8-methyl-6-nonenoyl-CoA is produced by the branched-chain fatty acid pathway and condensed with...

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Monoterpene

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pyrophosphate, which is formed from acetyl-CoA via the intermediacy of mevalonic acid in the HMG-CoA reductase pathway. An alternative, unrelated biosynthesis...

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Cornus officinalis

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plant and as a medicinal plant. The plant contains oleanolic acid and ursolic acid. Ursolic acid has shown in vitro protective effects on auditory cells...

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