88418-12-6

Basic information

• Product Name: (1aR)-4,5,6,7,7a,7bα-Hexahydro-6β-hydroxy-7α,7aα-dimethyl-1aα-(1-methylethenyl)naphth[1,2-b]oxiren-2(1aH)-one
• Synonyms: (1aR)-4,5,6,7,7a,7bα-Hexahydro-6β-hydroxy-7α,7aα-dimethyl-1aα-(1-methylethenyl)naphth[1,2-b]oxiren-2(1aH)-one;Sporogen AO-1
• CAS NO: 88418-12-6
• Molecular Formula: C₁₅H₂₀O₃
• Molecular Weight: 248.3175
• Mol File: 88418-12-6.mol
• Article Data: 2

Chemical Properties

• Boiling Point: 384.3°Cat760mmHg
• Flash Point: 141.4°C
• Appearance: /
• Density: 1.17g/cm³
• Vapor Pressure: 1.73E-07mmHg at 25°C
• Refractive Index: 1.555
• CAS DataBase Reference: (1aR)-4,5,6,7,7a,7bα-Hexahydro-6β-hydroxy-7α,7aα-dimethyl-1aα-(1-methylethenyl)naphth[1,2-b]oxiren-2(1aH)-one(CAS DataBase Reference)
• NIST Chemistry Reference: (1aR)-4,5,6,7,7a,7bα-Hexahydro-6β-hydroxy-7α,7aα-dimethyl-1aα-(1-methylethenyl)naphth[1,2-b]oxiren-2(1aH)-one(88418-12-6)
• EPA Substance Registry System: (1aR)-4,5,6,7,7a,7bα-Hexahydro-6β-hydroxy-7α,7aα-dimethyl-1aα-(1-methylethenyl)naphth[1,2-b]oxiren-2(1aH)-one(88418-12-6)

Safety Data

• Hazardous Substances Data: 88418-12-6(Hazardous Substances Data)

Usage

Description

Sporogen-AO 1 is a fungal metabolite originally isolated from A. oryzae that has diverse biological activities. It inhibits HIV-1 Tat transactivation in a cell-based assay with an IC50 value of 15.8 μM. Sporogen-AO 1 is cytotoxic to HeLa, KB, and NCI H187 cancer cells (IC50s = 8.3, 9, and 5.1 μM, respectively). It is active against C. albicans (MIC = 4 mM).

InChI:InChI=1/C15H20O3/c1-8(2)15-12(17)7-10-5-6-11(16)9(3)14(10,4)13(15)18-15/h7,9,11,13,16H,1,5-6H2,2-4H3/t9-,11+,13+,14+,15-/m0/s1

Upstream product

• 122074-99-1 (4aR,5R,6R)-3-acetyl-6-tert-butyldimethylsilyloxy-5,6,7,8-tetrahydro-4a,5-dimethyl-2(4aH)naphthalenone 
• 122052-55-5 (3RS,4aR,5R,6R)-6-tert-butyldimethylsilyloxy-4,4a,5,6,7,8-hexahydro-3-(1'-hydroxyethyl)-4a,5-dimethyl-2(3H)naphthalenone 
• 122075-00-7 (3RS,4aR,5R,6R)-3-acetyl-6-tert-butyldimethylsilyloxy-4,4a,5,6,7,8-hexahydro-4a,5-dimethyl-2(3H)naphthalenone 
• 122052-54-4 (2R,3R,4R)-4-((tert-butyldimethylsilyl)oxy)-2,3-dimethyl-2-(3-oxobutyl)cyclohexan-1-one 
• 122052-66-8 (4aR,5R,6R)-(+)-6-(tert-butyldimethylsiloxy)-4a,5-dimethyl-4,4a,5,6,7,8-hexahydro-3H-naphthalen-2-one 
• 122074-98-0 (3R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-2,3-dimethyl-1-trimethylsilanyloxy-cyclohexene 
• 122052-53-3 (2R,3R,4R)-(-)-4-(tert-butyldimethylsiloxy)-2,3-dimethylcyclohexanone 
• 122052-57-7 (3S,4R,4aR,5R,6R)-3-acetyl-6-tert-butyldimethylsilyloxy-3,4-epoxy-4,4a,5,6,7,8-hexahydro-4a,5-dimethyl-2(3H)naphthalenone 
• 608-43-5 2,3-dimethyl-1,4-dihydroxybenzene 
• 111210-64-1 (3S,4R,4aR,5R,6R)-3-acetyl-3,4-epoxy-4,4a,5,6,7,8-hexahydro-4a,5-dimethyl-6-(tetrahydropyran-2-yloxy)-2(3H)-naphthalenone 
• 111210-62-9 (4aR,5R,6R)-3-acetyl-5,6,7,8-tetrahydro-4a,5-dimethyl-6-(tetrahydropyran-2-yloxy)-2(4aH)-naphthalenone 
• 111210-60-7 (3RS,4aR,5R,6R)-3-acetyl-4,4a,5,6,7,8-hexahydro-4a,5-dimethyl-6-(tetrahydropyran-2-yloxy)-2(3H)-naphthalenone 
• 111210-59-4 (3RS,4aR,5R,6R)-4,4a,5,6,7,8-hexahydro-3-(1-hydroxyethyl)-4a,5-dimethyl-6-(tetrahydropyran-2-yloxy)-2(3H)-naphthalenone 
• 111210-47-0 (4aR*,5R*,6R*)-4,4a,5,6,7,8-hexahydro-4a,5-dimethyl-6-(tetrahydropyran-2-yloxy)-2(3H)-naphthalenone 

Downstream Products

• 85431-61-4 (+)-phaseolinone 
• 55785-58-5 (3R,4R,5R,6R,7R)-phomenone 
• 125140-03-6 (1aS,6R,7R,7aR,7bR)-6-Hydroxy-7,7a-dimethyl-1a-((S)-2-methyl-oxiranyl)-4,5,6,7,7a,7b-hexahydro-1aH-1-oxa-cyclopropa[a]naphthalen-2-one 
• 125140-03-6 (+)-gigantenone 

Relevant articles and documents

EFFICIENT SYNTHESIS OF NATURAL ENANTIOMER OF SPOROGEN-AO 1 (13-DESOXYPHOMENONE), A SPOROGENIC SESQUITERPENE FROM ASPERGILLUS ORYZAE

An efficient total synthesis of (+)-sporogen-AO 1 (13-desoxyphomenone) 1 was achieved in 20 steps from ethyl (1R,2S)-5,5-ethylenedioxy-2-hydroxycyclohexanecarboxylate 3 in 8.3percent overall yield.The optically active 3 with 98.4percent e.e. was easily ob