76375-62-7

Basic information

• Product Name: [5R,(+)]-5-[(S)-1-Hydroxyethyl]-3-[(2S)-3-methyloxirane-2-yl]furan-2(5H)-one
• Synonyms: [5R,(+)]-5-[(S)-1-Hydroxyethyl]-3-[(2S)-3-methyloxirane-2-yl]furan-2(5H)-one;Asperlactone;(5R)-5-[(1S)-1-Hydroxyethyl]-3-[(2S,3S)-3-methyl-2-oxiranyl]-2(5H)-furanone
• CAS NO: 76375-62-7
• Molecular Formula: C9H12O4
• Molecular Weight: 184.19
• Mol File: 76375-62-7.mol

Chemical Properties

• Boiling Point: 381.1°C at 760 mmHg
• Flash Point: 158.3°C
• Appearance: /
• Density: 1.329g/cm³
• Vapor Pressure: 2.24E-07mmHg at 25°C
• Refractive Index: 1.549
• CAS DataBase Reference: [5R,(+)]-5-[(S)-1-Hydroxyethyl]-3-[(2S)-3-methyloxirane-2-yl]furan-2(5H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: [5R,(+)]-5-[(S)-1-Hydroxyethyl]-3-[(2S)-3-methyloxirane-2-yl]furan-2(5H)-one(76375-62-7)
• EPA Substance Registry System: [5R,(+)]-5-[(S)-1-Hydroxyethyl]-3-[(2S)-3-methyloxirane-2-yl]furan-2(5H)-one(76375-62-7)

Safety Data

• Hazardous Substances Data: 76375-62-7(Hazardous Substances Data)

Usage

Uses

Asperlactone is a biologically active polyketide metabolite produced mainly from aspergillus.

InChI:InChI=1/C9H12O4/c1-4(10)7-3-6(9(11)13-7)8-5(2)12-8/h3-5,7-8,10H,1-2H3/t4-,5-,7+,8+/m0/s1

Upstream product

• 79562-15-5 <2-(2)H3,2-(13)C>acetic acid 
• 17398-00-4 aspyrone 

Downstream Products

• 91793-94-1 Phenyl-carbamic acid (S)-1-[(R)-4-((2S,3S)-3-methyl-oxiranyl)-5-oxo-2,5-dihydro-furan-2-yl]-ethyl ester 
• 91793-95-2 4-Nitro-benzoic acid (S)-1-[(R)-4-((2S,3S)-3-methyl-oxiranyl)-5-oxo-2,5-dihydro-furan-2-yl]-ethyl ester 

Relevant articles and documents

The Biosynthesis of Asperlactone: Incorporation Studies with Acetate

The C-7 methyl group of asperlactone (1) retains up to two hydrogens from acetate; the involvement of intermediates in which this carbon forms part of an aromatic ring is thus discounted.

Chlorohydroaspyrones A and B, antibacterial aspyrone derivatives from the marine-derived fungus Exophiala sp.

Chlorohydroaspyrones A (1) and B (2), antibacterial aspyrone derivatives, and the previously described aspyrone (3), asperlactone (4), and penicillic acid (5) have been isolated from the broth of a marine isolate of the fungus Exophiala. The structure and absolute stereochemistry of the compounds were determined on the basis of the physicochemical data analysis and chemical reactions. Compounds 1 and 2 exhibited a mild antibacterial activity against Staphylococcus aureus, methicillin-resistant S. aureus, and multidrug-resistant S. aureus. The MIC values of each strain are as follows: compound 1 showed 62.5 μg/mL for S. aureus and 125 μg/mL for methicillin-resistant S. aureus and multidrug-resistant S. aureus, and compound 2, 62.5 μg/mL for S. aureus and methicillin-resistant S. aureus and 125 μg/mL for multidrug-resistant S. aureus.