24462-48-4

Basic information

• Product Name: D:C-Friedoolean-8-en-3β-ol
• Synonyms: D:C-Friedoolean-8-en-3β-ol;Isomultiflorenol
• CAS NO: 24462-48-4
• Molecular Formula: C30H50O
• Molecular Weight: 426.7174
• Mol File: 24462-48-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: D:C-Friedoolean-8-en-3β-ol(CAS DataBase Reference)
• NIST Chemistry Reference: D:C-Friedoolean-8-en-3β-ol(24462-48-4)
• EPA Substance Registry System: D:C-Friedoolean-8-en-3β-ol(24462-48-4)

Safety Data

• Hazardous Substances Data: 24462-48-4(Hazardous Substances Data)

Upstream product

• 26892-63-7 multiflorenol 
• 22611-25-2 isomultiflorenyl acetate 
• 143183-38-4 bryonolic acid acetate 
• 462101-96-8 Acetic acid (3S,4aR,6bS,8aS,11R,12aR,12bS,14bS)-11-formyl-4,4,6b,8a,11,12b,14b-heptamethyl-1,2,3,4,4a,5,6,6b,7,8,8a,9,10,11,12,12a,12b,13,14,14b-icosahydro-picen-3-yl ester 
• 63043-86-7 alnus-5(10)-en-3β-ol 
• 6449-21-4 alnus-5(10)-en-3β-yl acetate 
• 5957-66-4 dendropanoxide 
• 92542-02-4 5α,10α-epoxyalnusan-3β-yl acetate 
• 89950-02-7 multiflora-5,8-dien-3β-yl acetate 
• 96563-58-5 5-α,10α-epoxyalnusan-3β-ol 
• 96563-57-4 alnus-5(10)-en-3β-yl benzoate 
• 96563-59-6 5α,10α-epoxyalnusan-3β-yl benzoate 
• 177354-94-8 (2R,4aS,6aS,8aR,10S,12aS,14aS,14bR)-10-hydroxy-2,4a,6a,9,9,12a,14a-heptamethyl-1,2,3,4,4a,5,6,6a,7,8,8a,9,10,11,12,12a,13,14,14a,14b-icosahydropicene-2-carboxylic acid 
• 24480-43-1 (2R,4aS,6aS,8aR,10S,12aS,14aS,14bR)-methyl 10-hydroxy-2,4a,6a,9,9,12a,14a-heptamethyl-1,2,3,4,4a,5,6,6a,7,8,8a,9,10,11,12,12a,13,14,14a,14b-icosahydropicene-2-carboxylate 

Downstream Products

• 22611-26-3 Isomultiflorenon 

Relevant articles and documents

BIOSYNTHESIS OF BRYONOLIC ACID IN CULTURED CELLS OF WATERMELON

Bryonolic acid, a pentacyclic triterpene having an anti-allergic activity, was biosynthesized from R-mevalonate or acetate administered to cell cultures of watermelon (citrullus lanatus).The radioactivity of the labelled mevalonate added to cell-free extracts in the presence of ATP, Mg2+ adn NADPH was also incorporated into bryonolic acid as well as into the possible intermediates, isomultiflorenol, bryonolol and bryonolal.Furthermore, 2,2-oxidosqualene added to the microsomal solution of the same cell-free extracts was converted enzymatically into isomultiflorenol, which is converted to be the first cyclization product in the biosynthesis of bryonolic acid.These results indicate that bryonolic acid is biosynthesized from 2,3-oxidosqualene via isomultiflorenol and subsequent oxidations of the methyl group at C-29.

Relative population of S-form and F-form conformers of bryonolic acid and its derivatives in equilibrium in CDCl3 solutions

Relative populations of S-form (D-E rings: boat-boat form) and F-form (D-E rings: chair-chair form) conformers, in equilibrium in CDCl3 solutions, of 20 derivatives (2-21) of bryonolic acid (D:C-friedoolean-8-en-3 β-ol-29-oic acid) (1) were calculated from NMR spectral data (J-values and chemical shifts), with the aid of molecular mechanic calculation using a MM2/CONFLEX program system. The principal deciding factor of the population ratio was found to be whether the functionality at C-29 is trigonal or tetrahedral; the S-form : F-form was 0:100-32:68 for the "trigonal" type and 48:52-100:0 for the "tetrahedral." The reliability of the results is discussed.

Boron Trifluoride Etherate-catalyzed Backbone Rearrangement of 5α, 10α-Epoxyalnusan-3β-yl Acetate and Partial Synthesis of Isomultiflorenol

Epoxidation of alnus-5(10)-en-3β-yl acetate with m-chloroperbenzoic acid gave a 5α,10α-epoxide, treatment of which with boron trifluoride etherate afforded multiflora-5,8-dien-3β-yl acetate.On hydrogenation and hydrolysis, the diene gave isomultiflorenol.

A PARTIAL SYNTHESIS OF ISOMULTIFLORENOL FROM DENDROPANOXIDE

Epoxidation of alnus-5(10)-en-3β-yl acetate (3) with m-chloroperbenzoic acid gave a 5α,10α-epoxide (4), which was subjected to the BF3*OEt2-catalyzed backbone rearrangement to afford multiflora-5,8-dien-3β-yl acetate (6) as a main product.Hydrogenation of the diene (6) followed by hydrolysis gave isomultiflorenol (1a).Keywords: dendropanoxide; 5α,10α-epoxyalnusan-3β-yl acetate; multiflora-5,8-dien-3β-yl acetate; isomultiflorenyl acetate; 5β-isomultiflorenol; epoxidation; backbone rearrangement; X-ray analysis.