Albrassitriol

* Please be kindly noted products are not for therapeutic use. We do not sell to patients.

Albrassitriol
Category Others
Catalog number BBF-04411
CAS 110557-39-6
Molecular Weight 254.37
Molecular Formula C15H26O3
Purity ≥98%

Online Inquiry

Description

It is a metabolite of Alternaria brassiae.

Specification

Synonyms (1R-(1alpha,4alpha,4aalpha,8abeta))-1,4,4a,5,6,7,8,8a-Octahydro-1-(hydroxymethyl)-2,5,5,8a-tetramethyl-1,4-naphthalenediol; 1,4-Naphthalenediol, 1,4,4a,5,6,7,8,8a-octahydro-1-(hydroxymethyl)-2,5,5,8a-tetramethyl-, (1R-(1alpha,4alpha,4aalpha,8abeta))-
Storage Store at -20°C
IUPAC Name (1S,4R,4aS,8aS)-4-(hydroxymethyl)-3,4a,8,8-tetramethyl-5,6,7,8a-tetrahydro-1H-naphthalene-1,4-diol
Canonical SMILES CC1=CC(C2C(CCCC2(C1(CO)O)C)(C)C)O
InChI InChI=1S/C15H26O3/c1-10-8-11(17)12-13(2,3)6-5-7-14(12,4)15(10,18)9-16/h8,11-12,16-18H,5-7,9H2,1-4H3/t11-,12-,14-,15+/m0/s1
InChI Key RWPFZPBMMIWKKY-NZBPQXDJSA-N

Properties

Appearance Amorphous Powder
Boiling Point 387.5±42.0°C at 760 mmHg
Melting Point 100-104°C
Density 1.1±0.1 g/cm3
Solubility Soluble in Methanol

Reference Reading

1. Synthesis of (-)-albrassitriol and (-)-6-epi-albrassitriol from (+)-larixol
Pavel F Vlad, Alexandru Ciocarlan, Mihai Coltsa, Carolina Edu, Andrei Biriiac, Alic Barba, Calin Deleanu, Alina Nicolescu, Michele D'Ambrosio, Aede de Groot Nat Prod Res. 2013;27(9):809-17. doi: 10.1080/14786419.2012.706297. Epub 2012 Jul 16.
A novel synthesis of natural drimanic compounds, (-)-albrassitriol (2) and (-)-6-epi-albrassitriol (3), has been carried out starting from an easily available labdane diterpenoid, (+)-larixol (1). In a two-step procedure, (+)-larixol (1) was converted into 14,15-bisnorlab-7-ene-6,13-dione (9), which was then submitted to a Norrish type II photochemical degradation yielding drim-7,9(11)-diene-6-one (10), whose treatment with OsO4 led selectively to the formation of drim-7-ene-9α,11-diol-6-one (12). The same compound was obtained by selective epoxidation of the C(9)-C(11) double bond in drim-7,9(11)-diene-6-one (10) with monoperphtalic acid. Treatment of the resulting mixture of α- and β-epoxides (13 and 14) with HClO4 yielded drim-7-ene-9α,11-diol-6-one (12). Reduction of the C6-carbonyl group in drim-7-ene-9α,11-diol-6-one (12) with LiAlH4 afforded (-)-albrassitriol (2) and (-)-6-epi-albrassitriol (3), 12.4% and 13.6% overall yields, respectively.
2. Three new drimane sesquiterpenoids from cultures of the fungus Penicillium sp
Jian-Hai Ding, Zhang-Gui Ding, Wei-Xun Chunyu, Jiang-Yuan Zhao, Hai-Bin Wang, Shi-Wei Liu, Fei Wang J Asian Nat Prod Res. 2017 Aug;19(8):780-785. doi: 10.1080/10286020.2016.1261830. Epub 2016 Nov 28.
Three new drimane sesquiterpenoids, 12-hydroxyalbrassitriol (1), drim-8(12)-en-6β,7α, 9α,11-tetraol (2), and drim-68(12)-dien-9α,11-diol (3), along with one known analog albrassitriol (4), were isolated from cultures of the tin mine tailings-associated fungus Penicillium sp. The new structures were determined on the basis of extensive spectroscopic analyses. All compounds were tested for their cytotoxicities against five human cancer cell lines.

Recommended Products

Bio Calculators

Stock concentration: *
Desired final volume: *
Desired concentration: *

L

* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2

* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O c22h30n40
g/mol
g

Recently viewed products

Online Inquiry

Verification code

Copyright © 2024 BOC Sciences. All rights reserved.

cartIcon
Inquiry Basket