13065-22-0

Basic information

• Product Name: 7-(2-hydroxypropan-2-yl)-1,4a-dimethyloctahydronaphthalen-2(1H)-one
• CAS NO: 13065-22-0
• Molecular Formula: C₁₅H₂₆O₂
• Molecular Weight: 238.3657
• Mol File: 13065-22-0.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 338.8°C at 760 mmHg
• Flash Point: 144.1°C
• Density: 1.006g/cm³
• Vapor Pressure: 6.48E-06mmHg at 25°C
• Refractive Index: 1.491
• CAS DataBase Reference: 7-(2-hydroxypropan-2-yl)-1,4a-dimethyloctahydronaphthalen-2(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 7-(2-hydroxypropan-2-yl)-1,4a-dimethyloctahydronaphthalen-2(1H)-one(13065-22-0)
• EPA Substance Registry System: 7-(2-hydroxypropan-2-yl)-1,4a-dimethyloctahydronaphthalen-2(1H)-one(13065-22-0)

Safety Data

• Hazardous Substances Data: 13065-22-0(Hazardous Substances Data)

Upstream product

• 83093-41-8 (S)-7-(1,2-Dihydroxy-1-methyl-ethyl)-1,4a-dimethyl-4,4a,5,6-tetrahydro-3H-naphthalen-2-one 
• 83093-43-0 (1S,4aS,7R,8aS)-7-(1,2-Dihydroxy-1-methyl-ethyl)-1,4a-dimethyl-octahydro-naphthalen-2-one 
• 87059-23-2 Toluene-4-sulfonic acid 2-((2R,4aS,8aS)-4a,8-dimethyl-7-oxo-decahydro-naphthalen-2-yl)-2-hydroxy-propyl ester 
• 87059-24-3 (1S,4aS,7R,8aS)-1,4a-Dimethyl-7-(2-methyl-oxiranyl)-octahydro-naphthalen-2-one 
• 69427-76-5 eudesm-4-ene-3β,11-diol 
• 163276-51-5 11-hydroxy-4-eudesmadien-3-one 
• 36128-95-7 4-epi-aubergenone 
• 13065-22-0 (1R,4aS,7R)-7-(1-Hydroxy-1-methyl-ethyl)-1,4a-dimethyl-octahydro-naphthalen-2-one 
• 69366-16-1 (1S,4aS,7R,8aS)-7-(1-Hydroxy-1-methyl-ethyl)-1,4a-dimethyl-decahydro-naphthalen-2-ol 
• 69366-16-1 4α,5α-eudesmane-3β,11-diol 

Downstream Products

• 82462-29-1 2α-phenylseleno-11-hydroxy-4α,5α-eudesm-3-one 
• 13827-90-2 C₂₉H₄₂O₇S₂ 
• 87059-28-7 2-{(1R,3S,4S)-4-Methyl-3-[(S)-1-methyl-2-(2-nitro-phenylselanyl)-ethyl]-4-[2-(2-nitro-phenylselanyl)-ethyl]-cyclohexyl}-propan-2-ol 
• 87059-27-6 2-[(1R,3S,4S)-4-(2-Iodo-ethyl)-3-((S)-2-iodo-1-methyl-ethyl)-4-methyl-cyclohexyl]-propan-2-ol 
• 87059-26-5 (S)-2-[(1S,2S,5R)-2-(2-Hydroxy-ethyl)-5-(1-hydroxy-1-methyl-ethyl)-2-methyl-cyclohexyl]-propan-1-ol 
• 639-99-6 elemol 
• 69369-90-0 2α-phenylseleno-11-hydroxy-4β,5α-eudesm-3-one 
• 13085-25-1 trans-Dihydrocarisson-tosylhydrazon 

Relevant articles and documents

Stress metabolites of Solanum melongena: biosynthetic studies and isolation of auberganol and α- and β-eudesmol

Attempts to clarify the biosynthetic origin of the eggplant stress metabolite aubergenone (1) by incorporation of label from sodium acetate were frustrated by low yields and enrichment levels.However, the presence of deuterium in the biosynthetically significant 5-position was demonstrated by 2Hmr for the closely related auberganol (5) and α- and β-eudesmol (10 and 11), suggesting that these compounds, and hence also 1, are normal eudesmanes and not the products of a possible double rearrangement.Deuterium was also incorporated into the expected positions of 9-oxonerolidol (12), 9-oxynerolidol (13), and lubimin (4).Inco rporation of label from acetate could be determined satisfactorily only for 13 and its allylic isomer 14, corresponding with expectations.This is the first report of 5 as a natural product and of 10, 11, and the 10-epimer of 4 as eggplant stress metabolites.

Synthesis of Aubergenone, a Sesquiterpenoid Phytoalexin from Diseased Eggplants

The synthesis of aubergenone, a stress metabolite isolated from diseased eggplants, from α-cyperone, which implies revision of the assigned structure to the metabolite, is described.