419542-67-9

Basic information

• Product Name: (2-¹³C)benzyl acetate
• Synonyms: (2-¹³C)benzyl acetate
• CAS NO: 419542-67-9
• Molecular Weight: 151.166
• Mol File: 419542-67-9.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (2-¹³C)benzyl acetate(CAS DataBase Reference)
• NIST Chemistry Reference: (2-¹³C)benzyl acetate(419542-67-9)
• EPA Substance Registry System: (2-¹³C)benzyl acetate(419542-67-9)

Safety Data

• Hazardous Substances Data: 419542-67-9(Hazardous Substances Data)

Upstream product

• 100-39-0 benzyl bromide 
• 13291-89-9 [2-13C]-sodium acetate 
• 1563-80-0 (2-¹³C)acetic acid 
• 100-51-6 benzyl alcohol 

Downstream Products

• 1260236-99-4 1-benzyl 6-methyl [2-⁽¹³⁾C]-([1-⁽¹³⁾C]-2-acetyl)-3-oxohexanedioate 
• 419542-89-5 C₂₀⁽¹³⁾C₂H₃₂O₆ 
• 419542-71-5 benzyl [2-13C]-([2-13C]-2-methyl-1,3-dioxolan-2-yl)acetate 
• 419542-86-2 1-benzyl 6-tert-butyl-[2,3-13C₂]-3-oxohexanedioate 

Relevant articles and documents

A Branched Diterpene Cascade: The Mechanism of Spinodiene Synthase from Saccharopolyspora spinosa

A diterpene synthase from Saccharopolyspora spinosa was found to convert geranylgeranyl diphosphate into the new natural products spinodiene A and B, accompanied by 2,7,18-dolabellatriene. The structures and the formation mechanism of the enzyme products were investigated by extensive isotopic labelling experiments, which revealed an unusual branched isomerisation mechanism towards the neutral intermediate 2,7,18-dolabellatriene. A Diels–Alder reaction was used to convert the main diterpene product with its rare conjugated diene moiety into formal sesterterpene alcohols.

Nonactin biosynthesis: The initial committed step is the condensation of acetate (malonate) and succinate

Nonactin is a macrotetrolide antibiotic produced by Streptomyces griseus subsp. griseus ETH A7796 that has shown activity against the P170-glycoprotein efflux pump associated with multiple drug resistant cancer cells. Nonactin is a polyketide, albeit a highly atypical one. The structure is composed of two units of each of the enantiomers of nonactic acid, arranged in a macrocycle, so that the molecule has S4 symmetry and is achiral. The monomer units, (+)- and (-)-nonactic acid, are derived from acetate, succinate, and propionate, although the exact details of the assembly process are quite unclear. We have used feeding experiments with a series of multiple stable isotope labeled precursors to elucidate the details of the first committed step of nonactic acid biosynthesis. We have found that the 13C label from 3-ketoadipate is incorporated specifically into both nonactic acid and its homologue, homononactic acid. The data conclusively show that the first committed step of nonactin biosynthesis is the coupling of a succinate derivative with either acetate or malonate. The differentiation into either nonactate or homononactate occurs after the initial condensation; the homologues are not derived from use of a different "starter unit" by the nonactate polyketide synthase. The first step of nonactin biosynthesis involves achiral intermediates; differentiation between the known enantiocomplementary biosynthesis pathways to form each enantiomer of the precursor monomer units likely occurs after the initial condensation reaction.