5986-39-0

Basic information

• Product Name: (3β)-20,24-Epoxydammarane-3,25-diol
• Synonyms: (3β)-20,24-Epoxydammarane-3,25-diol;Ocotillol
• CAS NO: 5986-39-0
• Molecular Formula: C30H52O3
• Molecular Weight: 460.73208
• Mol File: 5986-39-0.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (3β)-20,24-Epoxydammarane-3,25-diol(CAS DataBase Reference)
• NIST Chemistry Reference: (3β)-20,24-Epoxydammarane-3,25-diol(5986-39-0)
• EPA Substance Registry System: (3β)-20,24-Epoxydammarane-3,25-diol(5986-39-0)

Safety Data

• Hazardous Substances Data: 5986-39-0(Hazardous Substances Data)

Upstream product

• 43128-36-5 trevoagenin B 3,30-diacetate 
• 54878-46-5 trevoagenin B 3-acetate 
• 50657-16-4 trevoagenin A 
• 50894-69-4 trevoagenin B 
• 54878-47-6 Acetic acid (3S,5R,8R,9R,10R,13R,14S,17S)-14-formyl-17-[(2S,5R)-5-(1-hydroxy-1-methyl-ethyl)-2-methyl-tetrahydro-furan-2-yl]-4,4,8,10-tetramethyl-16-oxo-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester 
• 5986-39-0 3-epiocotillol 
• 19132-84-4 ocotillone 

Downstream Products

• 5986-39-0 ocotillol 
• 5244-35-9 Acetic acid (3S,5R,8R,9R,10R,14R,17S)-17-[(2S,5R)-5-(1-hydroxy-1-methyl-ethyl)-2-methyl-tetrahydro-furan-2-yl]-4,4,8,10,14-pentamethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester 
• 19132-84-4 ocotillone 
• 5244-35-9 Acetic acid (3R,5R,8R,9R,10R,14R,17S)-17-[(2S,5R)-5-(1-hydroxy-1-methyl-ethyl)-2-methyl-tetrahydro-furan-2-yl]-4,4,8,10,14-pentamethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester 

Relevant articles and documents

DAMMARANE GLYCOSIDES FROM AERIAL PARTS OF NEOALSOMITRA INTEGRIFOLIOLA

From the aerial parts of Neoalsomitra integrifoliola, a new 20,24-epoxydammarane triterpene and 11 new glycosides were isolated along with a known cucurbitacin glycosides, seven known cucurbitacins and neoalsoside A.The latter compound has previously been isolated from the rhizomes of this plant.The structures of the mew compounds have been established by spectroscopic and chemical means. - Key words: Neoalsomitra integrifoliola; Cucurbitaceae; aerial parts; dammarane glycosides; neoalsosides A2, A3, A4, A5, C1, C2, D1, E1, F1, G1 and H1; neoalsogenins B, C, G and H; 20,24-epoxydammarane triterpenes.

Dammarane Triterpenes of Trevoa trinervis: Structure and Absolute Stereochemistry of Trevoagenins A, B, and C

Trevoagenins A, B, and C, extracted from Trevoa trinervis Miers, are shown, by chemical and spectral means, to be isomeric dammarane triterpenes posessing the general 3β,25,30-trihydroxy-(20,24)-epoxydammaran-16-one structure with stereoisomeric side-chains of the ocotillol type.Trevoagenin A (20R,24R)-(1),, whose stereochemistry has been esteblished by chemical methods and confirmed by X-ray analysis, was transformed into (20R,24ξ)-ocotillone (26) and the C-24 stereochemistry was assigned as R.As a consequence, the C-24 stereochemistry for ocotillol-related compounds of the (20R)-series, unestablished so far, has been determined.The stereochemistry of trevoagenin B, (20S,24R)-(13), was established by chemical correlation with trevoagenin A.Moreover, trevoagenin B was transformed into ocotillol (20S,24R)-(21) and its recently questioned C-24 stereochemistry has been reaffirmed.Trevoagenin C, (20S,24S)-(17), is the C-24 isomer of trevoagenin B as shown by degradation of both compounds to the lactone (16).

TRITERPENOIDS FROM THE LEAVES OF Betula lanata

From the unsaponifiable fraction of an ethereal extract of the leaves of Betula lanata, in addition to 3-epiocotillol (I) we have isolated a new triterpene, 20(S),24(R)-epoxydammarane-3α,11α,25-triol (V) and also derivatives of it - the monoacetates at C-3 (II) and C-11 (III), and the monoketone at C-3 (IV).The structures of compounds (I-V) have been established on the basis of the results of physicochemical investigations.