39765-50-9

Basic information

• Product Name: Bryonolol
• Synonyms: Bryonolol;(3beta,20alpha)-13-Methyl-26-norolean-8-ene-3,29-diol
• CAS NO: 39765-50-9
• Molecular Formula: C30H50O2
• Molecular Weight: 442.7168
• Mol File: 39765-50-9.mol
• Article Data: 4

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Bryonolol(CAS DataBase Reference)
• NIST Chemistry Reference: Bryonolol(39765-50-9)
• EPA Substance Registry System: Bryonolol(39765-50-9)

Safety Data

• Hazardous Substances Data: 39765-50-9(Hazardous Substances Data)

Upstream product

• 143183-42-0 3-epibryonolol diacetate 
• 143183-46-4 3-epibryonolol 
• 143183-48-6 7-oxodihydrokarounidiol diacetate 
• 143183-44-2 D:C-friedo-olean-7-ene-3α,29-diol diacetate 
• 143183-45-3 D:C-friedo-olean-9(11)-ene-3α,29-diol diacetate 
• 143183-47-5 7-oxodihydrokarounidiol 
• 118117-33-2 karounidiol diacetate 
• 39765-51-0 bryonolol diacetate 
• 143183-37-3 3-oxo-D:C-friedo-olean-8-en-29-al 
• 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 

Relevant articles and documents

Conformation of Bryonolic Acid and Its Derivatives in CDCl3 Solution by 1H NMR and 13C NMR Spectroscopy

Comparison of the 1H and 13C chemical shift data of bryonolic acid (D:C-friedoolean-8-en-3β-ol-29-oic acid) and its derivatives (13 species) revealed that the conformational features of these compounds in CDCl3 solution depend on whether the functional groups at C-29 are trigonal, such as COOCH3, or tetrahedral, such as CH2OH.In order to study the conformational features of these two groups of compounds, vicinal coupling constants between the protons on the E rings of the methyl ester of D:C-friedoolean-8-en-29-oic acid, D:C-fridoolean-8-en-29-ol and its acetate were measured.Comparison of the results with the steric geometries to be expected from the molecular mechanics calculation for the E-ring moieties of these derivatives in the S form (D-E rings: boat-boat form) and the F form (D-E rings: chair-chair form) led to the conclusion that the compounds having a trigonal functional group at C-29 mainly adopt the S form, and those having a tetrahedral functional group at C-29 are present as mixtures of the S and F form in equilibrium in the solutions.KEY WORDS - Conformation D:C-friedoolean-8-enes Molecular mechanics calculation 1H and 13C NMR

Five D:C-friedo-oleanane triterpenes from the seeds of Trichosanthes kirilowii MAXIM. and their anti-inflammatory effects

Five triterpenes with a D:C-friedo-oleanane skeleton, D:C-friedo-oleana- 7,9(11)-diene-3β,29-diol (3-epikarounidiol), 7-oxo-D:C-friedo-olean-8-en- 3β-ol (7-oxoisomultiflorenol), 7-oxo-8β-D:C-friedo-olean-9(11)-ene-3α,29- diol, D:C-friedo-olean-8-ene-3α,29-diol (3-epibryonolol), and D:C-friedo- olean-8-ene-3β,29-diol (bryonolol), the first four of which are new naturally occurring compounds, were isolated from the seeds of Trichosanthes kirilowii MAXIM. The structures were determined by spectral and chemical methods. 3-Epikarounidiol, 7-oxoisomultiflorenol, and 3-epibryonolol showed marked inhibitory activity against 12-O-tetradecanoylphorbol-13-acetate (TPA)-induced ear inflammation in mice. The 50% inhibitory dose of these triterpenes for TPA-induced inflammation (1 μg) was 0.2-0.6 mg/ear.

7-Oxodihydrokarounidiol [7-oxo-D:C-friedo-olean-8-ene-3α,29-diol], novel triterpene from Trichosanthes kirilowii

The structure of 7-oxodihydrokarounidiol [7-oxo-D:C-friedo-olean-8-ene-3α,29-diol], isolated from the seeds of Trichosanthes kirilowii (Cucurbitaceae), was determined by chemical correlation with karounidiol [D:C-friedo-oleana-7,9(11)-diene-3α,29-diol] from the same source. Two other natural products, viz. bryonolic acid (3β-hydroxy-D:C-friedo-olean-8-en-29-oic acid) and bryononic acid (3-oxo-D:C-friedo-olean-8-en-29-oic acid), were also correlated with karounidiol.