(-)-Vanilmandelic acid

Base Information

• Chemical Name: (-)-Vanilmandelic acid
• CAS No.: 41093-71-4
• Molecular Formula: C₉H₁₀O₅
• Molecular Weight: 198.175
• UNII: M19V3799SB
• Nikkaji Number: J74.181G
• Wikidata: Q27283350
• Metabolomics Workbench ID: 166458
• ChEMBL ID: CHEMBL2074737
• Mol file: 41093-71-4.mol

Synonyms:(-)-Vanilmandelic acid;D-Vanillylmandelic acid;Vanilmandelic acid, D-;D(-)vanillylmandelic acid;Vanilmandelic acid, (-)-;Vanilmandelic acid, D-(-)-;Vanilmandelic acid D-form [MI];(R)-4-Hydroxy-3-methoxymandelic acid;(-)-4-Hydroxy-3-methoxymandelic acid;D-(-)-4-Hydroxy-3-methoxymandelic acid;M19V3799SB;41093-71-4;UNII-M19V3799SB;3-Methoxy-4-hydroxy-D-mandelic acid;SCHEMBL140947;Benzeneacetic acid,alpha,4-dihydroxy-3-methoxy-, (R)-;CHEMBL2074737;(2R)-2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)acetic acid;Benzeneacetic acid,alpha,4-dihydroxy-3-methoxy-, (alphaR)-;Q27283350;BENZENEACETIC ACID,.ALPHA.,4-DIHYDROXY-3-METHOXY-, (R)-;BENZENEACETIC ACID,.ALPHA.,4-DIHYDROXY-3-METHOXY-, (.ALPHA.R)-

Chemical Property of (-)-Vanilmandelic acid

Chemical Property:

• XLogP3: -0.2
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 198.05282342
• Heavy Atom Count: 14
• Complexity: 205

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=C(C=CC(=C1)C(C(=O)O)O)O
• Isomeric SMILES: COC1=C(C=CC(=C1)[C@H](C(=O)O)O)O

Technology Process of (-)-Vanilmandelic acid

There total 4 articles about (-)-Vanilmandelic 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:

4-hydroxy-3-methoxy-mandelic acid (55-10-7,2394-20-9) → 3-methoxy-4-hydroxy mandelic acid (13244-77-4,2394-20-9) + 3-methoxy-4-hydroxy mandelic acid (41093-71-4,2394-20-9)

Guidance literature:

With (3R,4S)-4-(3,5-dinitrobenzamido)-1,2,3,4-tetrahydrophenanthren-3-yl covalently linked to 3-propyl silica surface; In hexane; acetic acid; isopropyl alcohol; at 25 ℃; pH=3.6; Resolution of racemate;

DOI:10.1002/chir.20767

Reference yield:

4-hydroxy-3-methoxy-mandelic acid (55-10-7,2394-20-9) → 3-methoxy-4-hydroxy mandelic acid (41093-71-4,2394-20-9)

Guidance literature:

With (R)-ketoacid reductase from Saccharomyces cerevisiae ZJB₅₀₇₄; (S)-hydroxyacid dehydrogenase from Pseudomonas aeruginosa CCTCC M 2011394; glycerol; In aq. phosphate buffer; at 30 ℃; for 21h; pH=7.5; enantioselective reaction; Enzymatic reaction;

DOI:10.1039/c3cc46240d

Reference yield:

(4-hydroxy-3-methoxy-phenyl)-glyoxylic acid (2021-40-1) → 3-methoxy-4-hydroxy mandelic acid (41093-71-4,2394-20-9)

Guidance literature:

With (R)-ketoacid reductase from Saccharomyces cerevisiae ZJB₅₀₇₄; glycerol; In aq. phosphate buffer; at 30 ℃; pH=7.5; enantioselective reaction; Enzymatic reaction;

DOI:10.1039/c3cc46240d

upstream raw materials:

4-hydroxy-3-methoxy-mandelic acid

(4-hydroxy-3-methoxy-phenyl)-glyoxylic acid

Downstream raw materials:

(R)-2-(3,4-dimethoxyphenyl)-2-hydroxyethanamide