(2S)-2-hydroxyhexanoic acid

Base Information

• Chemical Name: (2S)-2-hydroxyhexanoic acid
• CAS No.: 70267-26-4
• Molecular Formula: C6H12O3
• Molecular Weight: 132.159
• UNII: 43W9KLV3ZE
• Nikkaji Number: J231.884I
• Wikidata: Q27896724
• Metabolomics Workbench ID: 166399
• Mol file: 70267-26-4.mol

Synonyms:(2S)-2-hydroxyhexanoic acid;70267-26-4;(s)-2-hydroxyhexanoic acid;Hexanoic acid, 2-hydroxy-, (2S)-;L-2-hydroxycaproic acid;L-2-hydroxyhexanoic acid;(S)-2-Hydroxycaproic acid;43W9KLV3ZE;2-Hydroxyhexanoic acid, (-)-;2-Hydroxyhexanoic acid, (2S)-;UNII-43W9KLV3ZE;(2S)-2-hydroxyhexanoicacid;SCHEMBL360108;(S)-alpha-Hydroxycaproic acid;AKOS006377819;(S)-.ALPHA.-HYDROXYCAPROIC ACID;F79866;EN300-1132067;Q27896724

Chemical Property of (2S)-2-hydroxyhexanoic acid

Chemical Property:

• Melting Point: 59 - 60 °C
• PSA: 57.53000
• LogP: 0.62210
• XLogP3: 1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 132.078644241
• Heavy Atom Count: 9
• Complexity: 90.3

Purity/Quality:

99%min ^*data from raw suppliers

(S)-2-Hydroxyhexanoicacid 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCCC(C(=O)O)O
• Isomeric SMILES: CCCC[C@@H](C(=O)O)O

Technology Process of (2S)-2-hydroxyhexanoic acid

There total 13 articles about (2S)-2-hydroxyhexanoic 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: 96.7%

L-Norleucine (327-57-1) → (S)-2-hydroxyhexanoic acid (70267-26-4)

Guidance literature:

With acetic acid; sodium nitrite; In water; Ambient temperature;

DOI:10.1080/00397919108055449

Reference yield: 95.0%

(S)-2-acetoxyhexanoic acid → (S)-2-hydroxyhexanoic acid (70267-26-4)

Guidance literature:

(S)-2-acetoxyhexanoic acid; With methanol; potassium carbonate; at 0 ℃;

With hydrogenchloride; In methanol; water; pH=2 - 3; optical yield given as %ee;

DOI:10.1016/j.tet.2009.06.051

Reference yield: 48.0%

vinyl acetate (108-05-4,9003-20-7) + rac-2-hydroxyhexanoic acid (636-36-2,6064-63-7) → (S)-2-acetoxyhexanoic acid + (R)-2-hydroxyhexanoic acid (43201-07-6) + (S)-2-hydroxyhexanoic acid (70267-26-4)

Guidance literature:

With acrylic resin immobilized Candida antarctica lipase; In tert-butyl methyl ether; at 20 ℃; optical yield given as %ee; Enzymatic reaction;

DOI:10.1016/j.tet.2009.06.051

upstream raw materials:

(S)-2-acetoxy-hexanoic acid ethyl ester

L-Norleucine

(R)-hydroxy-[2]thienyl-acetic acid

1-iodo-butane

Downstream raw materials:

pentanal

rac-2-hydroxyhexanoic acid

(S)-benzyl 2-(2-hydroxyhexanamido)acetate

(6S,1'S)-6-(1'-benzyloxypentyl)-5,6-dihydropyran-2,4(3H)-dione

Refernces

• 1、 Masuda, Masahiro,Nishimura, Ki-i-chi. "ABSOLUTE CONFIGURATIONS OF QUERCUS LACTONES, (3S,4R)- AND (3S,4S)-3-METHYL-4-OCTANOLIDE, FROM OAK WOOD AND CHIROPTICAL PROPERTIES OF MONO-CYCLIC χ-LACTONES". . p. 1333 - 1336. Retrieved 1981.
• 2、 Busto, Eduardo,Grischek, Barbara,Kroutil, Wolfgang,Richter, Nina. "Biocontrolled formal inversion or retention of L -α-amino acids to enantiopure (R)- or (S)-hydroxyacids". supporting information. p. 11225 - 11228,4. Retrieved 2015/01/07.
• 3、 Bodlenner, Anne,Glueck, Silvia M.,Nestl, Bettina M.,Gruber, Christian C.,Baudendistel, Nina,Hauer, Bernhard,Kroutil, Wolfgang,Faber, Kurt. "Biocatalytic racemization of α-hydroxycarboxylic acids using a stereo-complementary pair of α-hydroxycarboxylic acid dehydrogenases". experimental part. p. 7752 - 7755. Retrieved 2009/12/04.