10048-32-5

Basic information

• Product Name: PARASORBICACID
• Synonyms: PARASORBICACID;(S)-6-Methyl-5,6-dihydro-2H-pyran-2-one;[S,(+)]-5,6-Dihydro-6-methyl-2H-pyran-2-one;Parascorbic acid
• CAS NO: 10048-32-5
• Molecular Formula: C₆H₈O₂
• Molecular Weight: 112.14
• Mol File: 10048-32-5.mol

Chemical Properties

• Boiling Point: bp14 104-105°; bp22 119-123°
• Flash Point: 86°C
• Appearance: /
• Density: d418 1.079
• Vapor Pressure: 0.0765mmHg at 25°C
• Refractive Index: nD25 1.4682
• CAS DataBase Reference: PARASORBICACID(CAS DataBase Reference)
• NIST Chemistry Reference: PARASORBICACID(10048-32-5)
• EPA Substance Registry System: PARASORBICACID(10048-32-5)

Safety Data

• Hazardous Substances Data: 10048-32-5(Hazardous Substances Data)

Usage

Safety Profile

Poison by intraperitoneal and intravenous routes. Mildly toxic by skin contact. Questionable carcinogen with experimental neoplas tigenic data. When heated to decomposition it emits acrid smoke and irritating fumes.

InChI:InChI=1/C6H8O2/c1-5-3-2-4-6(7)8-5/h2,4-5H,3H2,1H3/t5-/m0/s1

Upstream product

• 106353-63-3 (S)-3,5-Dihydroxy-hexanoic acid ethyl ester 
• 201230-82-2 carbon monoxide 
• 207129-91-7 (S)-((pent-4-yn-2-yloxy)methyl)benzene 
• 105729-35-9 5-(tert-Butyl-dimethyl-silanyloxy)-3-oxo-hexanoic acid methyl ester 
• 1018700-57-6 methyl 3,5-dihydroxyhexanoate 
• 650596-62-6 (-)-(S)-5-hydroxy-2-hexynoic acid ethyl ester 
• 91273-88-0 Z-methyl (5S)-5-((tetrahydro-2H-pyran-2-yl)oxy)hex-2-enoate 
• 137449-09-3 5-(tert-Butyl-dimethyl-silanyloxy)-3-hydroxy-hexanoic acid methyl ester 
• 132604-16-1 3-(1-Hydroxy-3-oxo-butylidene)-1,5-dioxa-spiro[5.5]undecane-2,4-dione 
• 132604-17-2 3-((S)-1,3-Dihydroxy-butylidene)-1,5-dioxa-spiro[5.5]undecane-2,4-dione 
• 84257-12-5 2,2-dimethyl-5-(1-hydroxy-3-oxobutylidene)-1,3-dioxane-4,6-dione 
• 132604-10-5 5-((3S)-1,3-dihydroxybutylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 132604-11-6 (S)-5,6-dihydro-4-hydroxy-6-methyl-2H-pyran-2-one 
• 109462-44-4 (R)-3-hydroxy-5-hexenoic acid methyl ester 

Downstream Products

• 43112-32-9 (R)-(+)-δ-methyl-δ-valerolactone 
• 16320-13-1 (S)-6-methyl-tetrahydro-pyran-2-one 
• 139209-88-4 (R)-5-Hydroxy-hexanoic acid ((R)-1-phenyl-ethyl)-amide 
• 139209-88-4 (S)-5-Hydroxy-hexanoic acid ((R)-1-phenyl-ethyl)-amide 

Relevant articles and documents

Asymmetric synthesis of goniothalamin, hexadecanolide, massoia lactone, and parasorbic acid via sequential allylboration-esterification ring-closing metathesis reactions

Acrylic esters of homoallylic alcohols prepared in 92-97% ee via the asymmetric allylboration of appropriate aldehydes with B- allyldiisopinocampheylborane, when refluxed in dichloromethane in the presence of 10 mol% of Grubbs' catalyst provided the natural enantiomers of (S)-(+)-parasorbic acid, (R)-(-)-massoia lactone, and (R)-(+)goniothalamin. (S)-(-)-Hexadecanolide was prepared by hydrogenating the corresponding lactenone synthesized using the above sequence. (C) 2000 Elsevier Science Ltd.

ALLYLSILANES IN ORGANIC SYNTHESIS; STEREOSELECTIVE HYDROXYLACTONISATION OF CHIRAL AMIDE-ALLYLSILANES

The amide-allylsilanes (1) and (10) undergo stereoselective hydroxylactonisation on treatment with m-CPBA; the major products from (1) and (10) were converted into parasorbic acid (9) and the carpenter bee pheromone (13) respectively.

Synthesis of γ- and δ-lactone natural products by employing a trans-cis isomerization/lactonization strategy

Alkaline hydrolysis of 4-hydroxy- or/and 5-hydroxy-(2E)-alkenoate followed by acid treatment gave the corresponding (2E)-alkenoic acids which were subjected to lactone formation reaction without further purification. The crude acids were treated with 2,4,6-trichlorobenzoyl chloride in pyridine to afford ?-lactone or d-lactone, respectively, accompanied by trans-cis isomerization. By this procedure, (±)-(4,5)-trans-5-benzyloxy- 2-hexen-4-olide (90% overall yield), (S)-5-hydroxy-2-penten-4-olide (86% overall yield), (4S,5R)-5- hydroxy-2-hexen-4-olide (86% overall yield), (4R,5S)-5-hydroxy-2-hexen-4-olide (82% overall yield), (S)- parasorbic acid (58% overall yield) and natural product, (5R,7S)-7-hydroxy-2-octen-5-olide (euscapholide: 20% overall yield) were synthesized.

SYNTHESIS OF PARASORBIC ACID, THE COMPONENT OF SORBUS AUKUPARIA L.

Parasorbic acid ((5s)-(+)-hexen-5-olide) was synthesized from ethyl acetoacetate by utilizing its baker's yeast reduction.

Baker's Yeast Mediated Bioreduction of Prochiral Ketones Having 6-(4-Oxo-1,3-dioxinyl) Group

Prochiral ketones having 6-(4-oxo-1,3-dioxinyl) group as one terminal unit by fermenting baker's yeast gave chiral alcohols, which could be convertible to optically active hydroxyesters, β-ketoesters, and lactones.

Synthetic studies on marineosins based on a direct coupling reaction of pyrrole and δ-lactone

A promising precursor of marineosins A and B, unusual macrocyclic pyrrole and spiroiminal alkaloids isolated from marine microorganism has been synthesized employing a direct coupling of pyrrole and δ-lactone.

Twofold polyketide branching by a stereoselective enzymatic Michael addition

The versatility of the branching module of the rhizoxin polyketide synthase was tested in an in vitro enzyme assay with a polyketide mimic and branched (di)methylmalonyl-CoA extender units. Comparison of the products with synthetic reference compounds revealed that the module is able to stereoselectively introduce two branches in one step by a Michael addition-lactonisation sequence, thus expanding the scope of previously studied PKS systems.

Enantiomerically pure allylboronic esters as versatile reagents in the enantioselective synthesis of dihydro-α-pyrone-containing natural products

A short and efficient enantio- and diastereoselective synthesis of different representatives from the class of dihydro-α-pyrone natural products, including both enantiomers of goniothalamin, massoia lactone, parasorbic acid, and some derivatives is presented. It is based on the application of enantiopure α-chiral allylboronic esters in allyl additions. Georg Thieme Verlag Stuttgart New York.

Enantioselective synthesis of the 3C-protease inhibitor (-)-thysanone by a Staunton-Weinreb annulation strategy

The total synthesis of (-)-thysanone is described. The key step involves the addition of an o-toluate anion to a lactone to create the naphthopyran framework (Staunton-Weinreb annulation). This synthesis further confirms the absolute stereochemistry of th

One-pot and sequential asymmetric hydrogenation of β,δ-diketoesters into functionalized 1,3-diols: From anti- to syn-stereoselectivity

The asymmetric hydrogenation of methyl 3,5-dioxohexanoate (1) into mixtures of 3,5-dihydroxyesters (2) and 3-hydroxylactones (3) has been reinvestigated with a variety of ruthenium catalysts. Catalysts bearing diphosphanes which possess axial chirality such as (S)-MeO-Biphep give predominantly (3R,5S)-anti-2 in up to 78% de and 95% ee, affording an efficient synthesis of (S)-6-methyl-5,6-dihydro-2-pyrone [(S)-5] in up to 95% enantiomeric excess. On the contrary, some Ru-{amidophosphane-phosphinite} complexes catalyze sluggishly the formation of syn-2 in up to 92% de but with poor enantiomeric excesses. In all cases, methyl (R)-3-hydroxy-5-oxohexanoate [(R)-11] is the exclusive primary hydrogenation product, which can be isolated in high yields and enantiomeric excesses up to 78%. Further hydrogenation of enantiomerically enriched (R)-11 in a separate experiment affords (3R,5R)-syn-2 in high diastereomeric and enantiomeric excesses (up to 80% and 98%, respectively), provided a Ru-(R)-Binap-type catalyst is used.