(2R)-2-hydroxyhexanoic acid

Base Information

• Chemical Name: (2R)-2-hydroxyhexanoic acid
• CAS No.: 43201-07-6
• Molecular Formula: C6H12O3
• Molecular Weight: 132.159
• European Community (EC) Number: 873-254-0
• UNII: 54ADS710JF
• Nikkaji Number: J231.883K
• Wikidata: Q27896714
• Mol file: 43201-07-6.mol

Synonyms:(2R)-2-hydroxyhexanoic acid;(r)-2-hydroxyhexanoic acid;43201-07-6;D-2-hydroxycaproic acid;d-2-hydroxyhexanoic acid;(R)-2-Hydroxycaproic acid;54ADS710JF;2-Hydroxyhexanoic acid, (+)-;2-Hydroxyhexanoic acid, (2R)-;Hexanoic acid, 2-hydroxy-, (2R)-;UNII-54ADS710JF;(R)-alpha-Hydroxycaproic acid;SCHEMBL4378353;NYHNVHGFPZAZGA-RXMQYKEDSA-N;(R)-.ALPHA.-HYDROXYCAPROIC ACID;CS-0312132;F79865;EN300-1174620;Q27896714;Z1205493801;7N6

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

Chemical Property:

• Melting Point: 62 °C
• Boiling Point: 270.0±0.0 °C(Predicted)
• PKA: 3.86±0.21(Predicted)
• PSA: 57.53000
• Density: 1.100±0.06 g/cm3(Predicted)
• 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:

98% ^*data from raw suppliers

(R)-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 (2R)-2-hydroxyhexanoic acid

There total 15 articles about (2R)-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: 93.0%

2-oxo-hexanoic acid sodium salt (13022-85-0) → (R)-2-hydroxyhexanoic acid (43201-07-6)

Guidance literature:

With phosphate buffer; D-glucose; 2-hydroxyethanethiol; sodium chloride; formate dehydrogenase; 1,4-dihydronicotinamide adenine dinucleotide; benzoylformate reductase; bovine serum albumin; yeast alcohol dehydrogenase; In ethanol; water; toluene; at 30 ℃; for 24h;

Reference yield: 87.3%

D-norleucine (327-56-0) → (R)-2-hydroxyhexanoic acid (43201-07-6)

Guidance literature:

With sulfuric acid; sodium nitrite; at 0 - 20 ℃; for 22h;

DOI:10.1016/S0040-4020(02)00099-6

Reference yield: 82.0%

L-Norleucine (327-57-1) → (R)-2-hydroxyhexanoic acid (43201-07-6)

Guidance literature:

With formate dehydrogenase; oxygen; ammonium formate; NADH; In aq. phosphate buffer; at 21 ℃; for 7h; under 750.075 Torr; pH=7; stereoselective reaction; Enzymatic reaction;

DOI:10.1002/chem.201403195

upstream raw materials:

D-norleucine

1-iodo-butane

2-hydroxyhexanoic acid ethyl ester

rac-2-hydroxyhexanoic acid

Downstream raw materials:

(5S)-N-[5-chloro-2-(1H-tetrazol-1-yl)benzyl]-1-[(2R)-2-hydroxyhexanoyl]-4,5-dihydro-1H-pyrazole-5-carboxamide

(R)-benzyl 2-(2-hydroxyhexanamido)acetate

2-({2-[3-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-propyl]-4,5-dipentyl-phenyl}-methyl-amino)-hexanoic acid benzyl ester

2-({2-[3-(tert-butyl-dimethyl-silanyloxy)-2-hydroxy-propyl]-5-octyl-phenyl}-methyl-amino)-hexanoic acid benzyl ester

Refernces

• 1、 Dennig, Alexander,Gandomkar, Somayyeh,Cigan, Emmanuel,Reiter, Tamara C.,Haas, Thomas,Hall, Mélanie,Faber, Kurt. "Enantioselective biocatalytic formal α-amination of hexanoic acid to l-norleucine". supporting information. p. 8030 - 8033. Retrieved 2018/11/23.
• 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.