638-97-1

Basic information

• Product Name: 18BETA(H)-OLEAN-12-EN-3-ONE
• Synonyms: 18BETA(H)-OLEAN-12-EN-3-ONE;Olean-12-en-3-one;β-Amyrone;beta-Amyrone;beta-AMyrenone
• CAS NO: 638-97-1
• Molecular Formula: C₃₀H₄₈O
• Molecular Weight: 424.7
• Mol File: 638-97-1.mol

Chemical Properties

• Melting Point: 177-178 °C
• Boiling Point: 488.3 °C at 760 mmHg
• Flash Point: 202.8 °C
• Appearance: /
• Density: 1.01 g/cm³
• Vapor Pressure: 1.1E-09mmHg at 25°C
• Refractive Index: 1.534
• Storage Temp.: 2-8°C
• CAS DataBase Reference: 18BETA(H)-OLEAN-12-EN-3-ONE(CAS DataBase Reference)
• NIST Chemistry Reference: 18BETA(H)-OLEAN-12-EN-3-ONE(638-97-1)
• EPA Substance Registry System: 18BETA(H)-OLEAN-12-EN-3-ONE(638-97-1)

Safety Data

• Hazardous Substances Data: 638-97-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
18BETA(H)-OLEAN-12-EN-3-ONE is used as an inhibitor of cyclooxygenase and lipoxygenase enzymes for studying the structure-activity relationships of pentacyclic triterpenoids. This application is significant in understanding the molecular mechanisms underlying various diseases and developing targeted therapeutic strategies.
Used in Chemical Industry:
In the chemical industry, 18BETA(H)-OLEAN-12-EN-3-ONE can be utilized as a starting material or intermediate for the synthesis of various compounds with potential applications in different fields, such as agrochemicals, fragrances, and cosmetics. Its unique structure and reactivity make it a valuable component in the development of novel products and formulations.

InChI:InChI=1/C30H48O/c1-25(2)15-16-27(5)17-18-29(7)20(21(27)19-25)9-10-23-28(6)13-12-24(31)26(3,4)22(28)11-14-30(23,29)8/h9,21-23H,10-19H2,1-8H3/t21-,22?,23-,27-,28+,29-,30-/m1/s1

Upstream product

• 559-70-6 beta-amyrin 
• 559-70-6 β-amyrin 
• 108335-08-6 olean-12-en-3-O-β-D-galactopyranosyl(1->4)-O-α-L-rhamnopyranoside 
• 152487-61-1 (3β)-3-{[(1,1-dimethylethyl)dimethylsilyl]oxy}-olean-12-en-28-ol 
• 197500-50-8 (4aS,6aS,6bR,8aR,10S,12aR,12bR,14bS)-10-(tert-Butyl-dimethyl-silanyloxy)-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-octadecahydro-2H-picene-4a-carboxylic acid methyl ester 
• 107596-78-1 olean-12-ene-3-ol 
• 18674-44-7 3-Methoxy-1-oxo-oleanadien-(2,12) 
• 18674-43-6 1,3-Dioxoolean-12-en 
• 67173-33-5 oleana-1,12-dien-3-one 

Downstream Products

• 471-68-1 olean-12-ene 
• 559-70-6 beta-amyrin 
• 6811-63-8 3α-hydroxyolean-12-ene 
• 2935-32-2 3,11-dioxo-β-amyrene 
• 144268-61-1 [(4aR,6aR,6bS,8aR,12aR,14aR,14bR)-4,4,6a,6b,8a,11,11,14b-Octamethyl-1,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-octadecahydro-2H-picen-(3E)-ylidene]-hydrazine 
• 3399-27-7 olean-13⁽¹⁸⁾-ene 
• 107596-89-4 18αH-olean-12-ene 
• 61235-46-9 (6aR,6bS,8aR,14bR)-4,4,6a,6b,8a,11,11,14b-Octamethyl-1,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-octadecahydro-picene-2,3-dione 
• 85031-74-9 2-oximino-β-amyrone 
• 640-25-5 oleana-2,12-diene 
• 1616-93-9 β-amyrin acetate 
• 108354-98-9 (4aS,6aS,6bR,8aR,12aS,12bR,14bR)-2,2,4a,6a,6b,9,9,12a-Octamethyl-1,4,4a,5,6,6a,6b,7,8,8a,9,12a,12b,14b-tetradecahydro-2H-picene-3,10,13-trione 
• 108354-97-8 (4aR,6aR,6bS,8aS,12aS,14aR,14bS)-4,4,6a,6b,8a,11,11,14b-Octamethyl-4a,5,6,6a,6b,7,8a,9,10,11,12,12a,14a,14b-tetradecahydro-4H-picene-3,8,14-trione 
• 108376-34-7 oleana-1,12-diene-3,11-dione 

Relevant articles and documents

COMPOSITIONS COMPRISING TRITERPENOIDS

The invention relates to compositions and formulations comprising at least one triterpenoic acid and at least one neutral triterpenoid and uses thereof for treating for use in treating a condition selected from Alzheimer's disease (AD), Parkinson's Diseases (PD) and vascular dementia (VD).

Chemical constituents of Psychotria nemorosa gardner and antinociceptive activity

Through dereplication strategies using gas chromatography-mass spectrometry (GC-MS) and ultra fast liquid chromatography-tandem mass spectrometry (UFLC-MS/MS), the ethanol extract from Psycotria nemorosa leaves (Rubiaceae) showed to be composed of: cinnamic acid, dihydroactinidiolide, 4-hydroxy-β-ionone, phytol, isophytol, 4,8,12,16-tetramethylheptadecan- 4-olide, lupeol, a mixture of α/β-amyrin, the keto and acetylated derivatives, besides stigmast- 4-en-3-one, campesterol, stigmasterol and γ-sitosterol by GC-MS. Likewise, by UFLC-MS/MS, the main compounds identified were: butin, resveratrol, rutin, kaempferol 7-O-β-D-glucopyranoside, deacetylasperuloside, epiloganin, hordenine, strictosidine, N-methyl-1,2,3,4-tetrahydro-β-carboline and N-formyl-tryptamine. The antinociceptive activity of the crude extract ant its fractions was reported.

Differentiation- and apoptosis-inducing activities by pentacyclic triterpenes on a mouse melanoma cell line

In a study to investigate the relationship between the chemical structure and the differentiation-inducing activity of pentacyclic triterpenes, several lupane, oleanane, and ursane triterpenes were prepared and their effects on B16 2F2 melanoma cell differentiation and growth were examined. Eleven lupane triterpenes used in this study acted on the melanoma cells as a melanogen, but no induction of melanogenesis of B16 2F2 cells by oleanane and ursane was detected. The differences at C-17 of the lupane series and acetylation of the OH group at C-3 did not markedly influence their activities. However, the ED50 value for up-regulation of melanin biosynthesis was markedly decreased by the oxidation of the OH group at C-3 of lupeol (1). Betulinic acid (11), its methyl ester (12), lup-28-al-20(29)-ene-3β-ol (9), and lup-28-al-20(29)-en-3-one (10) inhibited B16 2F2 cell proliferation by induction of apoptosis. These findings suggested that the carbonyl group at C-17 might be essential for the apoptotic effects of these compounds on B16 2F2 cells.

Biomimetic oxidation of 3β-hydroxy-olean-12-ene and its acetoxy derivative with monooxygen donors catalyzed by 5,10,15,20-tetraarylporphyrinatoiron(III) chlorides in dichloromethane

The oxidation of 3β-hydroxy-olean-12-ene with monooxygen donors catalyzed by 5,10,15,20-tetraarylporphyrinatoiron(III) chlorides in dichloromethane gives 3β,11α-dihydroxy-olean-12-ene, 3-oxo-olean-12-ene, 3,11-dioxo-olean-12-ene and 3β-hydroxy-olean-9(11),12-diene whereas the oxidation of 3β-acetoxy-olean-12-ene under similar conditions gives 11(-hydroxy-3β-acetoxy-olean-12-ene, 11-oxo-3β-acetoxy-olean-12-ene and 3β-acetoxy-olean-9(11),12-diene in moderate yields.

Olean-12-en-3-O-β-D-galactopyranosyl(1->4)-O-α-L-rhamnopyranoside: A New Triterpenoidal Saponin from the roots of Spilanthes acmella (Murr.).

A new triterpenoidal saponin has been isolated from the roots of Spilanthes acmella (Murr.) and characterized as olean-12-en-3-O-β-D-galactopyranosyl(1->4)-O-α-L-rhamnopyranoside on the basis of chemical and spectral studies.

DIHYDRONYCTANTHIC ACID METHYL ESTER AND OTHER 3,4-SECO-PENTACYCLIC TRITERPENOIDS FROM HOYA LACUNOSA

From the wax of old leaves of Hoya lacunosa was isolated a mixture of 4(23)-saturated seco-ring-A triterpene acid methyl esters.One of these compounds was identified as the β-amyrin derivative 5-isopropyl-10(2-methoxy-carbonylethyl)-des-A-olean-12-en (dihydronyctanthic acid methyl ester), while another compound was a raraxerol derivative 5-isopropyl-10(2-methoxycarbonylethyl)-des-A-olean-14-en.Two other constituents were probably derived from α-amyrin and taraxasterol, respectively.Key Word Index-Hoya lacunosa; Asclepiadaceae; leaf wax; 3,4-seco-pentacyclic triterpenoid acid methyl ester; dihydronyctanthic acid methyl ester.

Preparation of Triterpenoid Diosphenol via Oximinoketone and Structure of Baccatin

Diosphenols of lupane, moretene, β-amyrine and 28-norolean-12,17-diene have been prepared from the corresponding 3-keto compounds via 2-oximino derivatives.The oleanane skeleton of baccatin (I) has been confirmed by transforming it into 2,3-dioxo-28-nor-olean-12,17-dione (IIe).

TERPENOIDS OF CANARIUM ZEYLANICUM

The following terpenoids were identified in the oleoresin, bark and timber of Canarium zeylanicum: 3β-hydroxyurs-12-en-11-one, 3β-hydroxyolean-12-en-11-one, olean-12-en-3,11-dione, urs-12-en-3,11-dione, α- and β-amyrin, α- and β-amyrenone, taraxerol, sitosterol, canaric acid, elemene, elemol, α-pinene, α- and β-phellandrene, limonene, terpineol, and cavrone. - Key Word Index - Canarium zeylanicum; Burseraceae; oleoresin; bark; timber; monoterpenoids; sesquiterpenoids; triterpenoids; 3β-hydroxyurs-12-en-11-one (neoilexonol); 3β-hydroxyolean-12-en-11-one; olean-12-en-3,11-dione; urs-12-en-3,11-dione; elemene; elemol; α-amyrine and β-amyrine; α- and β-amyrenone; canaric acid; taraxerol; sitosterol.