Parasorbic acid

Base Information

• Chemical Name: Parasorbic acid
• CAS No.: 10048-32-5
• Molecular Formula: C₆H₈O₂
• Molecular Weight: 112.128
• Hs Code.: 2932999099
• UNII: DCN48OUK3T
• DSSTox Substance ID: DTXSID10893607
• Nikkaji Number: J51.180C
• Wikipedia: Parasorbic_acid
• Wikidata: Q27107618
• Metabolomics Workbench ID: 127510
• ChEMBL ID: CHEMBL2252704
• Mol file: 10048-32-5.mol

Synonyms:5-hydroxy-2-hexenoic acid delta lactone;parasorbic acid;parasorbic acid, (+-)-isomer;parasorbic acid, (S)-isomer

Chemical Property of Parasorbic acid

Chemical Property:

• Vapor Pressure: 0.0765mmHg at 25°C
• Refractive Index: 1.454
• Boiling Point: 227.7°C at 760 mmHg
• Flash Point: 86°C
• PSA: 26.30000
• Density: 1.045g/cm³
• LogP: 0.87800
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 112.052429494
• Heavy Atom Count: 8
• Complexity: 127

Purity/Quality:

98%,99%, ^*data from raw suppliers

PARASORBIC ACID 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC=CC(=O)O1
• Isomeric SMILES: C[C@H]1CC=CC(=O)O1

Technology Process of Parasorbic acid

There total 51 articles about Parasorbic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

Z-methyl (5S)-5-((tetrahydro-2H-pyran-2-yl)oxy)hex-2-enoate (91273-88-0,91273-89-1,91326-78-2) → (S)-parasorbic acid (10048-32-5)

Guidance literature:

With toluene-4-sulfonic acid; In dichloromethane; for 3h; Inert atmosphere; Schlenk technique;

DOI:10.1039/c5cc03085d

Reference yield: 91.0%

(S)-3,6-dihydro-6-methyl-2H-pyran-2-one (93338-33-1) → (S)-parasorbic acid (10048-32-5)

Guidance literature:

With diazabicyclo<5.4.0>undecene; In tetrahydrofuran; at 25 ℃; for 4h;

DOI:10.1016/0008-6215(84)85235-0

Reference yield: 90.0%

(S)-4-Hydroxy-6-methyl-tetrahydro-pyran-2-one (233255-67-9) → (S)-parasorbic acid (10048-32-5)

Guidance literature:

With toluene-4-sulfonic acid; In benzene; Heating;

DOI:10.1016/S0040-4039(00)88516-0

upstream raw materials:

3,5-dioxohexanoic acid methyl ester

methyl 3,5-dihydroxyhexanoate

(S)-6-Methyl-4-(toluene-4-sulfonyl)-tetrahydro-pyran-2-one

(S)-4-Hydroxy-6-methyl-tetrahydro-pyran-2-one

Downstream raw materials:

(R)-5-Hydroxy-hexanoic acid ((R)-1-phenyl-ethyl)-amide

(S)-5-Hydroxy-hexanoic acid ((R)-1-phenyl-ethyl)-amide

Refernces

• 1、 Russell, Andrew T.,Procter, Garry. "ALLYLSILANES IN ORGANIC SYNTHESIS; STEREOSELECTIVE HYDROXYLACTONISATION OF CHIRAL AMIDE-ALLYLSILANES". . p. 2041 - 2044. Retrieved 1987.
• 2、 Sato, Tsuguo. "SYNTHESIS OF PARASORBIC ACID, THE COMPONENT OF SORBUS AUKUPARIA L.". . p. 2173 - 2174. Retrieved 1986.
• 3、 Lichtenthaler, Frieder W.,Klingler, Franz D.,Jarglis, Pan. "Simple synthesis of (S)-parasorbic acid and other (5S)-hydroxy six-carbon synthons from L-rhamnose". . p. C1 - C4. Retrieved 1984.
• 4、 Heine, Daniel,Sundaram, Srividhya,Bretschneider, Tom,Hertweck, Christian. "Twofold polyketide branching by a stereoselective enzymatic Michael addition". supporting information. p. 9872 - 9875. Retrieved 2015/06/16.