6-epi-Albrassitriol
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| Category | Bioactive by-products |
| Catalog number | BBF-01790 |
| CAS | 178456-58-1 |
| Molecular Weight | 254.37 |
| Molecular Formula | C15H26O3 |
| Purity | 95% |
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Description
It is produced by the strain of Aspergillus sp. FH-A 6357. It has the inhibitory effect of cholesterol, and has weak anti-influenza virus A (MIC is 44 μg/mL) and sticky virus activity.
Specification
| Synonyms | 6-Epialbrassitriol; (1R,4S,4aS,8aS)-1-(hydroxymethyl)-2,5,5,8a-tetramethyldecahydronaphthalene-1,4-diol; 1,4-Naphthalenediol, 1,4,4a,5,6,7,8,8a-octahydro-1-(hydroxymethyl)-2,5,5,8a-tetramethyl-, (1R,4R,4aS,8aS)- |
| IUPAC Name | (1R,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-/m1/s1 |
| InChI Key | RWPFZPBMMIWKKY-PAPYEOQZSA-N |
Properties
| Appearance | Powder |
| Antibiotic Activity Spectrum | Viruses |
| Melting Point | 164 °C |
| Solubility | Soluble in Methanol, Ethanol, Acetone, Chloroform; Insoluble in N-hexane |
Reference Reading
1. Three new drimane sesquiterpenoids from cultures of the fungus Penicillium sp
Fei Wang,Shi-Wei Liu,Zhang-Gui Ding,Jiang-Yuan Zhao,Hai-Bin Wang,Wei-Xun Chunyu,Jian-Hai Ding J Asian Nat Prod Res . 2017 Aug;19(8):780-785. doi: 10.1080/10286020.2016.1261830.
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.
2. Synthesis of (-)-albrassitriol and (-)-6-epi-albrassitriol from (+)-larixol
Calin Deleanu,Andrei Biriiac,Alic Barba,Carolina Edu,Aede de Groot,Mihai Coltsa,Alexandru Ciocarlan,Michele D'Ambrosio,Pavel F Vlad,Alina Nicolescu Nat Prod Res . 2013;27(9):809-17. doi: 10.1080/14786419.2012.706297.
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.
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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 ╳
