2-Hydroxy-3-methylpentanoic acid

Base Information

• Chemical Name: 2-Hydroxy-3-methylpentanoic acid
• CAS No.: 488-15-3
• Molecular Formula: C₆H₁₂O₃
• Molecular Weight: 132.159
• European Community (EC) Number: 207-671-0
• DSSTox Substance ID: DTXSID70862016
• Nikkaji Number: J182.234I
• Wikidata: Q105236955
• Mol file: 488-15-3.mol

Synonyms:2-hydroxy-3-methylpentanoic acid;2-hydroxy-3-methylvaleric acid;2-hydroxy-3-methylvaleric acid, calcium salt, (2:1), (S-(R*,R*))-isomer;2-hydroxy-3-methylvaleric acid, monosodium salt, (S-(R*,R*))-isomer;alpha-hydroxy-3-methylpentanoic acid

Chemical Property of 2-Hydroxy-3-methylpentanoic acid

Chemical Property:

• Vapor Pressure: 0.003mmHg at 25°C
• Melting Point: 50-53℃
• Boiling Point: 251.3°Cat760mmHg
• Flash Point: 120.1°C
• PSA: 57.53000
• Density: 1.097g/cm³
• LogP: 0.47800
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 132.078644241
• Heavy Atom Count: 9
• Complexity: 101

Purity/Quality:

99%, ^*data from raw suppliers

2-Hydroxy-3-methylpentanoicAcid(MixtureofDiastereomers) ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C)C(C(=O)O)O
• Uses: 2-Hydroxy-3-methylpentanoic Acid (Mixture of Diastereomers) can be used as a metabolite as a diagnostic for autism spectrum disorder in children with gastrointestinal symptoms.

Technology Process of 2-Hydroxy-3-methylpentanoic acid

There total 67 articles about 2-Hydroxy-3-methylpentanoic 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: 99.0%

L-isoleucine (73-32-5,959215-79-3,18875-42-8) → (2S,3S)-2-Hydroxy-3-methylpentanoic acid (488-15-3,59653-35-9,70748-47-9,86540-81-0,86630-77-5,51576-04-6)

Guidance literature:

With sulfuric acid; sodium nitrite; In water; at 0 - 20 ℃;

DOI:10.1016/j.tet.2016.03.079

Reference yield:

maedamide → (S)-2-Hydroxy-3-methylbutanoic acid (17407-55-5) + D-alloisoleucine (1509-35-9,959215-79-3,18875-42-8) + (2R,3S)-2-hydroxy-3-methylpentanoic acid (488-15-3,51576-04-6,59653-35-9,86540-81-0,86630-77-5,70748-47-9) + N-methyl-D-phenylalanine (56564-52-4) + L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7)

Guidance literature:

With hydrogenchloride; In water; at 110 ℃; for 25h;

DOI:10.1016/j.tetlet.2014.05.099

Reference yield:

odoamide → L-alanin (56-41-7,25191-17-7,18875-37-1) + N-methylalanine (3913-67-5) + L-isoleucine (73-32-5,959215-79-3,18875-42-8) + (2R,3S)-2-hydroxy-3-methylpentanoic acid (488-15-3,51576-04-6,59653-35-9,86540-81-0,86630-77-5,70748-47-9) + N-methyl-D-phenylalanine (56564-52-4)

Guidance literature:

With hydrogenchloride; In water; at 105 ℃; for 12h;

DOI:10.1016/j.tet.2016.07.031

upstream raw materials:

L-isoleucine

sulfuric acid

(2S)-2-methyl-1-butanol

(S)-2-methylbutyraldehyde

Downstream raw materials:

(E)-(S)-4-Methyl-hex-2-enoic acid benzyl ester

(S)-3-(4-Hydroxy-3-iodo-phenyl)-2-((2S,3S)-2-hydroxy-3-methyl-pentanoylamino)-propionic acid methyl ester

(2S,3S)-2-(benzyloxy)-3-methylpentanal

(2S,3S)-2-Benzyloxy-3-methyl-pentan-1-ol

Refernces

• 1、 Carter, Daniel C.,Moore, Richard E.,Mynderse, Jon S.,Niemczura, Walter P.,Todd, James S.. "Structure of Majusculamide C, a Cyclic Depsipeptide from Lyngbya majuscula". . p. 236 - 241. Retrieved 1984.
• 2、 Choi, Hyukjae,Pereira, Alban R.,Cao, Zhengyu,Shuman, Cynthia F.,Engene, Niclas,Byrum, Tara,Matainaho, Teatulohi,Murray, Thomas F.,Mangoni, Alfonso,Gerwick, William H.. "The hoiamides, structurally intriguing neurotoxic Lipopeptides from Papua New Guinea marine cyanobacteria". . p. 1411 - 1421. Retrieved 2010.
• 3、 Isaka, Masahiko,Palasarn, Somporn,Komwijit, Somjit,Somrithipol, Sayanh,Sommai, Sujinda. "Pleosporin A, an antimalarial cyclodepsipeptide from an elephant dung fungus (BCC 7069)". . p. 469 - 471. Retrieved 2014.
• 4、 Mimaki, Yoshihiro,Kuroda, Minpei,Kameyama, Aiko,Yokosuka, Akihito,Sashida, Yutaka. "New steroidal constituents of the underground parts of Ruscus aculeatus and their cytostatic activity on HL-60 cells". . p. 298 - 303. Retrieved 1998.
• 5、 Ehling-Schulz, Monika,Hofmann, Thomas F.,Kranzler, Markus,Stark, Timo D.,Walser, Veronika. "Structure revision of isocereulide A, an isoform of the food poisoning emetic Bacillus cereus toxin cereulide". supporting information. . Retrieved 2021/05/31.
• 6、 Kienle, Maryline,Eisenring, Patrick,Stoessel, Barbara,Horlacher, Oliver P.,Hasler, Samuel,Van Colen, Gwéna?lle,Hartkoorn, Ruben C.,Vocat, Anthony,Cole, Stewart T.,Altmann, Karl-Heinz. "Synthesis and Structure-Activity Relationship Studies of C2-Modified Analogs of the Antimycobacterial Natural Product Pyridomycin". . p. 1105 - 1131. Retrieved 2020/03/10.