51311-41-2

Basic information

• Product Name: A-factor (Streptomyces)
• Synonyms: A-factor (Streptomyces);(4R)-4-Hydroxymethyl-3-(6-methyl-1-oxoheptyl)-4,5-dihydrofuran-2(3H)-one;(4R)-4α-(Hydroxymethyl)-3-(6-methylheptanoyl)-4,5-dihydro-2(3H)-furanone;(4R)-Dihydro-3-(6-methylheptanoyl)-4α-(hydroxymethyl)furan-2(3H)-one;A-Factor【lactone】;2-isocapryloyl-3R-hydroxymethyl-gamma-butyrolactone
• CAS NO: 51311-41-2
• Molecular Formula: C₁₃H₂₂O₄
• Molecular Weight: 242.31138
• Mol File: 51311-41-2.mol

Chemical Properties

• Boiling Point: 410.4°Cat760mmHg
• Flash Point: 152.1°C
• Appearance: /
• Density: 1.074g/cm³
• Vapor Pressure: 1.9E-08mmHg at 25°C
• Refractive Index: 1.474
• CAS DataBase Reference: A-factor (Streptomyces)(CAS DataBase Reference)
• NIST Chemistry Reference: A-factor (Streptomyces)(51311-41-2)
• EPA Substance Registry System: A-factor (Streptomyces)(51311-41-2)

Safety Data

• Hazardous Substances Data: 51311-41-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
A-factor (Streptomyces) is used as a bioactive compound for its potential therapeutic effects. Its ability to modulate various cellular processes and interact with biopolymers and macromolecules makes it a promising candidate for the development of new drugs and therapies.
Used in Cosmetics Industry:
A-factor (Streptomyces) is used as an active ingredient in cosmetics for its potential skin care benefits. Its unique structure and biological activities may contribute to improving skin health, reducing inflammation, and promoting tissue repair.
Used in Research and Development:
A-factor (Streptomyces) is used as a research tool for studying the mechanisms of action and potential applications of butan-4-olides. Its unique structure and biological activities make it an interesting subject for further investigation and development in various scientific fields.
Used in Agricultural Industry:
A-factor (Streptomyces) is used as a biopesticide or biocontrol agent for its potential to control pests and diseases in agriculture. Its ability to modulate various biological processes may help in the development of environmentally friendly and effective pest control strategies.

InChI:InChI=1/C13H22O4/c1-9(2)5-3-4-6-11(15)12-10(7-14)8-17-13(12)16/h9-10,12,14H,3-8H2,1-2H3/t10-,12?/m1/s1

Upstream product

• 63098-10-2 (S)-3-(6-Methyl-heptanoyl)-4-trimethylsilanyloxymethyl-dihydro-furan-2-one 
• 54673-14-2 [(ethoxymethoxy)methyl]benzene 
• 27490-33-1 tri-n-butylstannylmethanol 
• 134665-20-6 2,2-Dimethyl-propionic acid (S)-4-(6-methyl-heptanoyl)-5-oxo-tetrahydro-furan-3-ylmethyl ester 
• 626-88-0 1-bromo-5-methylpentane 
• 55387-85-4 3-hydroxymethyl-4-hydroxybutanal diethyl acetal 
• 162662-07-9 (4R)-4-(((tert-butyldimethylsilyl)oxy)methyl)-3-(6-methylheptanoyl)dihydrofuran-2(3H)-one 
• 85701-08-2 (R)-4-(hydroxymethyl)dihydrofuran-2(3H)-one 
• 80656-73-1 (R)-3-(6-Methyl-heptanoyl)-4-trimethylsilanyloxymethyl-dihydro-furan-2-one 
• 80656-71-9 (S)-(+)-3-hydroxymethyl-4-butanolide 
• 80656-72-0 (R)-(-)-3-trimethylsilyloxymethyl-4-butanolide 
• 870-63-3 prenyl bromide 
• 934248-96-1 C₁₄H₂₂O₅ 
• 207444-47-1 (S)-4-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxymethyl]-3-(6-methyl-heptanoyl)-dihydro-furan-2-one 

Downstream Products

• 122876-18-0 (3R,4S)-4-[Dimethyl-(1-methyl-1-phenyl-ethyl)-silanyloxymethyl]-3-((S)-1-hydroxy-6-methyl-heptyl)-dihydro-furan-2-one 
• 122876-18-0 (3S,4S)-4-[Dimethyl-(1-methyl-1-phenyl-ethyl)-silanyloxymethyl]-3-((R)-1-hydroxy-6-methyl-heptyl)-dihydro-furan-2-one 
• 122876-19-1 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (R)-1-{(3S,4S)-4-[dimethyl-(1-methyl-1-phenyl-ethyl)-silanyloxymethyl]-2-oxo-tetrahydro-furan-3-yl}-6-methyl-heptyl ester 
• 122922-65-0 (R)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (S)-1-{(3R,4S)-4-[dimethyl-(1-methyl-1-phenyl-ethyl)-silanyloxymethyl]-2-oxo-tetrahydro-furan-3-yl}-6-methyl-heptyl ester 
• 122922-64-9 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (R)-1-{(3S,4S)-4-[dimethyl-(1-methyl-1-phenyl-ethyl)-silanyloxymethyl]-2-oxo-tetrahydro-furan-3-yl}-6-methyl-heptyl ester 
• 122922-66-1 (S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (S)-1-{(3R,4S)-4-[dimethyl-(1-methyl-1-phenyl-ethyl)-silanyloxymethyl]-2-oxo-tetrahydro-furan-3-yl}-6-methyl-heptyl ester 

Relevant articles and documents

Organocatalytic approach for short asymmetric synthesis of (r)-paraconyl alcohol: Application to the total syntheses of IM-2, SCB2, and a-factor γ-butyrolactone autoregulators

(R)-Paraconyl alcohol is found to be a key intermediate for the syntheses of many γ-butyrolactone autoregulators. The chiral auxiliary approach and enzymatic resolution are the two common strategies employed so far in the literature for the asymmetric syn

Replication of biosynthetic reactions enables efficient synthesis of A-factor, a γ-butyrolactone autoinducer from Streptomyces griseus

We report a concise synthesis of A-factor, the prototypical γ-butyrolactone signalling compound of Streptomyces bacteria. In analogy to enzymatic reactions in A-factor biosynthesis, our synthesis features a tandem esterification-Knoevenagel condensation yielding a 2-acyl butenolide and a surprising, chemoselective conjugate reduction of this α,β- unsaturated carbonyl compound using sodium cyanoborohydride.

Asymmetric synthesis of A-factor

The synthesis of enantlopure A-factor ['autoregulatory factor'; (3R)-(-)-2-(6-methylheptanoyl)-3-hydroxymethylbutano-4-lactone] by the completely diastereoselective benzyloxymethylation of (4R)-3-(3-phenylpropanoyl)-4-isopropyloxazolidin-2-one is reported.

Synthesis of Optically Active A-Factor

(3R)-(-)-A-factor and (3S)-(+)-A-factor are synthesised via the same chiral intermediate 6, the synthesis of which proceeds through a Johnson-Claisen rearrangement key step.

Regioselective synthesis of hydroxy butenolides: A convenient synthesis of A-factor

An elegant approach for the regioselective preparation of hydroxy butenolide by the oxidation of 2-ethoxyfuran with MnO2-HCl is described.

A Synthesis of 3-Hydroxymethyl-2-(6-methylheptanoyl)-4-butanolide (A-Factor)

The A-Factor was conveniently synthesized from 3-furoic acid via the Birch reduction.

Synthetic Microbial Chemistry, XXIII Synthesis of Optically Active Virginiae Butanolides A, B, C, and D and other Autoregulators from Streptomycetes

Optically active A-factor (1), the factor from Streptomyces viridochromogenes (2), the factors from S. bikiniensis and S. cyaneofuscatus (3-5), and virginiae butanolides A (6), B (7), C (8), and D (9) were synthesized starting from (S)-(-)-paraconic acid

ASYMMETRIC CONJUGATE ADDITIONS OF AN HYDROXYMETHYL CARBANION EQUIVALENT. SYNTHESIS OF (+)-A FACTOR

An effective procedure is presented for generation of Ph2CH2OCH2Li via tin -> lithium exchange and for conjugate addition of this HOCH2- equivalent to some homochiral cycloalkenone and butenolide sulfoxides.

SYNTHESIS OF OPTICALLY ACTIVE FORMS OF A-FACTOR, THE INDUCER OF STREPTOMYCIN BIOSYNTHESIS IN INACTIVE MUTANTS OF STREPTOMYCES GRISEUS

The absolute configuration at C-3 of A-factor, 2-(6-methylheptanoyl)-3-hydroxymethyl-4-butanolide 1a, was determined to be S by synthesizing both enantiomers of it from paraconic acid. (3S)-A-factor was 2.5 times more active than the (3R)-isomer as the inducer of streptomycin biosynthesis in inactive mutants of Streptomyces griseus.