Albrassitriol
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| Category | Others |
| Catalog number | BBF-04411 |
| CAS | 110557-39-6 |
| Molecular Weight | 254.37 |
| Molecular Formula | C15H26O3 |
| Purity | ≥98% |
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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.
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Bio Calculators
* 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 ╳
