2-Hydroxydodecanoic acid

Base Information

• Chemical Name: 2-Hydroxydodecanoic acid
• CAS No.: 2984-55-6
• Molecular Formula: C12H24O3
• Molecular Weight: 216.321
• Hs Code.: 2918199090
• European Community (EC) Number: 221-048-0
• NSC Number: 39025
• UNII: 62H8XD5QSU
• DSSTox Substance ID: DTXSID501021252
• Nikkaji Number: J205.277F
• Wikidata: Q27071900
• Pharos Ligand ID: CQXHXMN6JBLS
• Metabolomics Workbench ID: 1312
• ChEMBL ID: CHEMBL4278254
• Mol file: 2984-55-6.mol

Synonyms:2-Hydroxydodecanoic acid;2984-55-6;2-Hydroxylauric acid;hydroxylauric acid;2-hydroxy lauric acid;Dodecanoic acid, 2-hydroxy-;alpha-Hydroxy lauric acid;2-hydroxy-dodecanoic acid;Dodecanoic acid, hydroxy-;UNII-62H8XD5QSU;62H8XD5QSU;2-OH-C12;EINECS 221-048-0;NSC-39025;74355-65-0;alpha-hydroxylauric acid;D0T4BP;Dodecanoic acid,2-hydroxy-;SCHEMBL154529;GTPL5849;DL-2-HYDROXYLAURIC ACID;CHEMBL4278254;ALPHA HYDROXY LAURIC ACID;CHEBI:36211;(+/-)-2-hydroxydodecanoic acid;HYDROXYLAURIC ACID [INCI];DTXSID501021252;DL-2-HYDROXYDODECANOIC ACID;CAA98455;NSC39025;LMFA01050036;NSC 39025;.ALPHA.-HYDROXYDODECANOIC ACID;AKOS015146113;(+/-)-.ALPHA.-HYDROXYLAURIC ACID;HY-116731;CS-0066402;2-Hydroxydodecanoic acid, >=98% (capillary GC);J-017664;Q27071900;F1916-0236

Chemical Property of 2-Hydroxydodecanoic acid

Chemical Property:

• Vapor Pressure: 3.05E-06mmHg at 25°C
• Melting Point: 46-47 °C
• Refractive Index: 1.466
• Boiling Point: 348.5 °C at 760 mmHg
• PKA: 3.86±0.21(Predicted)
• Flash Point: 178.8 °C
• PSA: 57.53000
• Density: 0.987 g/cm³
• LogP: 2.96270
• Storage Temp.: 2-8°C
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly),
• XLogP3: 4.2
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 10
• Exact Mass: 216.17254462
• Heavy Atom Count: 15
• Complexity: 157

Purity/Quality:

99% ^*data from raw suppliers

(±)-2-HydroxydodecanoicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCCCCCCC(C(=O)O)O
• Uses: (8Z,11Z,14Z)-8,11,14-Heptadecatrienoic Acid, is a naturally occurring hydroxylated fatty acid that is found in Acinetobacter species. It acts as a partial agonist of free fatty acid receptor 1 (FFAR1/GPR40) and GPR84 receptors in vitro. It also inhibits bovine hepatic ligase (Ki = 4.4 μM) and mouse kidney mitochondrial medium-chain acyl-CoA synthetase by 48% at a concentration of 40 μM.

Technology Process of 2-Hydroxydodecanoic acid

There total 25 articles about 2-Hydroxydodecanoic 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: 95.0%

lauric acid (143-07-7) → 2-hydroxydodecanoic acid (2984-55-6,37639-47-7)

Guidance literature:

With P_450CLA; dihydrogen peroxide; In aq. phosphate buffer; ethanol; at 20 ℃; for 12.5h; pH=7.25; regioselective reaction; Enzymatic reaction;

DOI:10.1002/adsc.201801377

Reference yield: 93.0%

tridecanoic acid (638-53-9) → 2-hydroxydodecanoic acid (2984-55-6,37639-47-7) + 2-Hydroxytridecanoic acid (19790-87-5)

Guidance literature:

With P_450CLA; dihydrogen peroxide; In aq. phosphate buffer; ethanol; at 20 ℃; for 12.5h; pH=7.25; regioselective reaction; Enzymatic reaction;

DOI:10.1002/adsc.201801377

Reference yield: 90.0%

S-methyl 2-hydroxydodecanethioate (124838-44-4) → 2-hydroxydodecanoic acid (2984-55-6,37639-47-7)

Guidance literature:

With hydrogenchloride; sodium hydroxide; In methanol; water; for 1h; Heating;

DOI:10.1246/bcsj.62.2013

upstream raw materials:

2-bromododecanoic acid

α-Acetoxylaurinsaeure-n-butylester

2-bromododecanoyl chloride

2-Propionyloxy-dodecanoic acid ethyl ester

Downstream raw materials:

undecylaldehyde

2-trifluoromethanesulfonyloxy-dodecanoic acid benzyl ester

(R)-2-hydroxy-dodecanoic acid

benzyl (E,2R)-5-(decyloxy)-4-[(2-hydroxydodecanoyl)amino]pent-2-enoate

Refernces

• 1、 Jeanneau, Erwann,Queneau, Yves,Soulère, Laurent,Zhang, Qiang. "(2R)- and (2S)- 2-hydroxy- hexanoyl and octanoyl-L-homoserine lactones: New highly potent Quorum Sensing modulators with opposite activities". . . Retrieved 2020.
• 2、 Armbruster, Julia,Steinmassl, Mathilde,Müller Bogotá, Christina A.,Berg, Gabriele,Nidetzky, Bernd,Dennig, Alexander. "P450Jα: A New, Robust and α-Selective Fatty Acid Hydroxylase Displaying Unexpected 1-Alkene Formation". . p. 15910 - 15921. Retrieved 2020/10/29.
• 3、 Dennig, Alexander,Blaschke, Fabio,Gandomkar, Somayyeh,Tassano, Erika,Nidetzky, Bernd. "Preparative Asymmetric Synthesis of Canonical and Non-canonical a-amino Acids through Formal Enantioselective Biocatalytic Amination of Carboxylic Acids". supporting information. p. 1348 - 1358. Retrieved 2019/10/28.