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
• Article Data: 10

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

Description

A-factor (Streptomyces), also known as butan-4-olide, is a chemical compound derived from Streptomyces bacteria. It is characterized by its gamma-butyrolactone structure with an isocapryloyl substituent at position 2 and a hydroxymethyl substituent at position 3 (the 3R-stereoisomer). This unique structure endows A-factor with various biological activities and potential applications in different industries.

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 
• 70767-37-2 6-methyl-heptanoyl chloride 
• 85701-09-3 (S)-(-)-3-Trimethylsiloxymethyl-4-butanolide 
• 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 
• 207444-47-1 (S)-4-[Dimethyl-(1,1,2-trimethyl-propyl)-silanyloxymethyl]-3-(6-methyl-heptanoyl)-dihydro-furan-2-one 
• 626-89-1 4-Methyl-1-pentanol 
• 929-10-2 isooctanoic acid 
• 39953-95-2 (4-methyl-pentyl)-malonic acid diethyl ester 
• 85701-08-2 (R)-4-(hydroxymethyl)dihydrofuran-2(3H)-one 
• 626-88-0 1-bromo-5-methylpentane 
• 4694-66-0 (-)-(S)-5-oxotetrahydro-3-furancarboxylic acid 
• 168134-75-6 (S)-4-Acetoxy-3-((R)-4-isopropyl-2-oxo-oxazolidine-3-carbonyl)-butyric acid 

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

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.

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.