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Ursolic acid information


Ursolic acid
Names
IUPAC name
3β-Hydroxyurs-12-en-28-oic acid
Systematic IUPAC name
(1S,2R,4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-Hydroxy-1,2,6a,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
Prunol, Malol, β-Ursolic acid, NSC4060, CCRIS 7123, TOS-BB-0966[1]
Identifiers
CAS Number
  • 77-52-1 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:9908 checkY
ChEMBL
  • ChEMBL169 checkY
ChemSpider
  • 58472 checkY
ECHA InfoCard 100.000.941 Edit this at Wikidata
PubChem CID
  • 64945
UNII
  • P3M2575F3F checkY
CompTox Dashboard (EPA)
  • DTXSID70883221 Edit this at Wikidata
InChI
  • InChI=1S/C30H48O3/c1-18-10-15-30(25(32)33)17-16-28(6)20(24(30)19(18)2)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h8,18-19,21-24,31H,9-17H2,1-7H3,(H,32,33)/t18-,19+,21+,22-,23+,24+,27+,28-,29-,30+/m1/s1 checkY
    Key: WCGUUGGRBIKTOS-GPOJBZKASA-N checkY
  • InChI=1/C30H48O3/c1-18-10-15-30(25(32)33)17-16-28(6)20(24(30)19(18)2)8-9-22-27(5)13-12-23(31)26(3,4)21(27)11-14-29(22,28)7/h8,18-19,21-24,31H,9-17H2,1-7H3,(H,32,33)/t18-,19+,21+,22-,23+,24+,27+,28-,29-,30+/m1/s1
    Key: WCGUUGGRBIKTOS-GPOJBZKABB
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)[C@@H](C)[C@H](C)CC5
Properties
Chemical formula
C30H48O3
Molar mass 456.711 g·mol−1
Melting point 285 to 288 °C (545 to 550 °F; 558 to 561 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)
Infobox references

Ursolic acid (sometimes referred to as urson, prunol, malol, or 3β-hydroxyurs-12-en-28-oic acid), is a pentacyclic triterpenoid identified in the epicuticular waxes of apples as early as 1920 and widely found in the peels of fruits, as well as in herbs and spices like rosemary and thyme.

  1. ^ CID 64945 from PubChem

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Ursolic acid

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Ursolic acid (sometimes referred to as urson, prunol, malol, or 3β-hydroxyurs-12-en-28-oic acid), is a pentacyclic triterpenoid identified in the epicuticular...

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Oleanolic acid

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TA-65 2.2-fold, and maslinic acid 2-fold. Ursolic acid Betulinic acid Moronic acid Momordin (saponin), a glycoside of oleanolic acid List of phytochemicals...

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Corosolic acid

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Corosolic acid is a pentacyclic triterpene acid found in Lagerstroemia speciosa. It is similar in structure to ursolic acid, differing only in the fact...

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List of phytochemicals in food

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

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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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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:10.1016/0378-8741(95)90032-2...

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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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Diospyros kaki

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triterpenoid compounds such as α-amyrin, uvaol, ursolic acid, 19α-hydroxy ursolic acid and 19 α,24-dihydroxy ursolic acid can be isolated from the leaves of D....

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Prunella vulgaris

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oleanolic acid, rosmarinic acid, myristic acid, rutin, linoleic acid, ursolic acid, beta-sitosterol, lupeol, and tannins. Prunella is derived from 'Brunella'...

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Plantago major

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extender. Plantain contains phytochemicals including allantoin, aucubin, ursolic acid, flavonoids, and asperuloside. Plantain extract has been studied for...

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Paeonia lactiflora

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prominent stamens) The leaves of many cultivars are high in oleanolic and ursolic acid. Cis-epsilon-viniferin, trans-resveratrol, trans-resveratrol-4'-O-be...

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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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Amyrin

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plant 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...

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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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Betulinic acid

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Oleanolic acid Ursolic acid Moronic acid Chowdhury AR, Mandal S, Mittra B, Sharma S, Mukhopadhyay S, Majumder HK (July 2002). "Betulinic acid, a potent...

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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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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...

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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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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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Rosemary

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of phytochemicals, including rosmarinic acid, camphor, caffeic acid, ursolic acid, betulinic acid, carnosic acid, and carnosol. Rosemary essential oil contains...

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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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Ocimum tenuiflorum

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Satheesh, B; Saravanan, D (2012). "LC-MS Quantification of Rosmarinic Acid and Ursolic Acid in Theocimum Sanctumlinn. Leaf Extract (Holy Basil, Tulsi)". Journal...

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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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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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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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Verbena officinalis

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β-sitosterol, ursolic acid, oleanolic acid, 3-epiursolic acid, 3-epioleanolic acid and minor triterpenoids of derivatives of ursolic acid and oleanolic acids. Chromatographic...

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Polyphenol

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plants and structurally diverse. Polyphenols include flavonoids, tannic acid, and ellagitannin, some of which have been used historically as dyes and...

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Cannabis

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LEI-106 ML294 ML295 ML296 UCM710 WWL-70 ABHD12 Inhibitors: Betulinic acid Maslinic acid MAFP Oleanolic acid Orlistat (tetrahydrolipstatin) Ursolic acid...

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