(r)-Mandelic acid

Base Information

• Chemical Name: (r)-Mandelic acid
• CAS No.: 611-71-2
• Deprecated CAS: 14447-35-9
• Molecular Formula: C8H8O3
• Molecular Weight: 152.15
• Hs Code.: 29181980
• European Community (EC) Number: 210-276-6
• UNII: PPL7YW1M9W
• DSSTox Substance ID: DTXSID4046523
• Nikkaji Number: J43.326H
• Wikipedia: Mandelic_acid
• Metabolomics Workbench ID: 49852
• ChEMBL ID: CHEMBL292411
• Mol file: 611-71-2.mol

Synonyms:611-71-2;(R)-(-)-Mandelic acid;(r)-mandelic acid;(R)-2-Hydroxy-2-phenylacetic acid;D-Mandelic acid;D-(-)-MANDELIC ACID;(-)-Mandelic acid;D(-)-Mandelic acid;(2R)-2-hydroxy-2-phenylacetic acid;Mandelic acid, (R)-;D-2-Phenylglycolic acid;(-)-(R)-Mandelic acid;(R)-alpha-Hydroxyphenylacetic acid;R-(-)-Mandelic acid;Mandelic acid, D-;(-)-alpha-Hydroxyphenylacetic acid;(R)-alpha-Hydroxybenzeneacetic acid;(R)-(-)-Amygdalic Acid;(R)-Mandelsaeure;(R)-A-Hydroxyphenylacetic acid;(R)-Hydroxy(phenyl)acetic acid;UNII-PPL7YW1M9W;PPL7YW1M9W;CHEMBL292411;DTXSID4046523;CHEBI:17656;(2R)-hydroxy(phenyl)acetic acid;Hydroxy-Phenyl-Acetic Acid Anion;L-2-Hydroxy-2-phenylacetic acid;EINECS 210-276-6;mandelic_acid;(R)-2-Hydroxy-2-phenylacetate;Benzeneacetic acid, alpha-hydroxy-, (-)-;D(-)-mandelate;R(-)-Mandelic Acid;MFCD00064251;Benzeneacetic acid, alpha-hydroxy-, (alphaR)-;mandelic-acid;RMN;(2R)-Hydroxyphenylacetic Acid ((R)-Mandelic Acid);Benzeneacetic acid, .alpha.-hydroxy-, (.alpha.R)-;DTXCID2026523;R-(-) Mandelic acid;(2R)-2-hydroxy-2-phenylacetate;CAS-611-71-2;(L)-(+)-Mandelic acid;(-)-D-MANDELIC ACID;1mcz;1mdl;(-)-mandelate;NCGC00166022-01;d - mandelic acid;D-2-Phenylglycolate;Sertraline impurity E;D-mandelic acid(R-(-)-mandelic acid);D-(?)-Mandelic acid;(-)-(R)-Mandelate;R-(?)-Mandelic Acid;(r)(-)-mandelic acid;Maybridge1_004148;(r)-(-) mandelic acid;(R)-(+)-mandelic acid;(R)-a-Hydroxyphenylacetate;(R)-Hydroxyphenylaceticacid;(-)-a-Hydroxyphenylacetate;(R)-a-Hydroxybenzeneacetate;Hydroxy-phenyl-acetate anion;(R)-(-)- mandelic acid;(r)-(-)-d-mandelic acid;Oprea1_502663;cid_11914;SCHEMBL165161;(-)-alpha-Hydroxyphenylacetate;(R)-alpha-Hydroxyphenylacetate;(-)-a-Hydroxyphenylacetic acid;(R)-alpha-Hydroxybenzeneacetate;(R)-a-Hydroxybenzeneacetic acid;BDBM16421;HMS553E14;D,L-mandelic acid redetermination;HMS3650C13;(2R)-hydroxy(phenyl)ethanoic acid;(R)-(-)-Mandelic acid, 98%;HY-Y0585;STR08136;Tox21_112292;s9003;(2R)-HYDROXYPHENYLACETIC ACID;AKOS005256699;Tox21_112292_1;(2R)-2-hydroxy-2-phenyl-acetic acid;AC-2490;CCG-266220;CS-W020074;DB02280;(-)-(R)alpha-hydroxybenzeneacetic acid;(-)-(R) alpha-hydroxybenzeneacetic acid;NCGC00166022-02;(2R)-2-oxidanyl-2-phenyl-ethanoic acid;Benzeneacetic acid, alpha-hydroxy-, (R)-;AM20050151;M0662;(R)-.ALPHA.-HYDROXYBENZENEACETIC ACID;Benzeneacetic acid, .alpha.-hydroxy-, (R)-;C01983;D70151;EN300-100159;MLS-0090888.0001;D-(-)-Mandelic acid, purum, >=98.0% (T);D-(-)-Mandelic acid, puriss., >=99.0% (T);SR-01000946767;(R)-(-)-Mandelic acid, ReagentPlus(R), >=99%;SR-01000946767-1;W-105188;Q63390533;(R)-(-)-Mandelic acid, Vetec(TM) reagent grade, 98%;F1905-7046;SERTRALINE HYDROCHLORIDE IMPURITY E [EP IMPURITY];Z1255390767;08C65DF7-6DDF-44B3-9490-02A43D9D33C1;(R)-(-)-Mandelic acid, ChiPros(R), produced by BASF, 99%;Sertraline impurity E, European Pharmacopoeia (EP) Reference Standard

Chemical Property of (r)-Mandelic acid

Chemical Property:

• Appearance/Colour: white to light yellow crystal powder
• Vapor Pressure: 5.14E-05mmHg at 25°C
• Melting Point: 131-133 °C(lit.)
• Refractive Index: -153.5 ° (C=1, H2O)
• Boiling Point: 321.8 °C at 760 mmHg
• PKA: 3.37(at 25℃)
• Flash Point: 162.6 °C
• PSA: 57.53000
• Density: 1.321 g/cm³
• LogP: 0.80460
• Storage Temp.: Refrigerator
• Sensitive.: Light Sensitive
• Solubility.: 109.8g/l soluble
• Water Solubility.: It is partly soluble in water, freely soluble in isopropyl and ethyl alcohol.
• XLogP3: 0.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 152.047344113
• Heavy Atom Count: 11
• Complexity: 138

Purity/Quality:

99.0%, ^*data from raw suppliers

(R)-(-)-Mandelic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 41-36/37/38
• Safety Statements: 22-24/25-36-26-39-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(C(=O)O)O
• Isomeric SMILES: C1=CC=C(C=C1)[C@H](C(=O)O)O
• Uses: (R)-(-)-Mandelic acid, is used as a antiseptic ingredient particularly against urinary tract infections.Mandelic acid and its derivatives are used to apply the dual activities as an antibacterial agent and as an antiaging agent. It is used as an intermediate for the synthesis of target molecules for other applications. (R)-(?)-Mandelic acid can be used:As a chiral acid in the separation of diastereomeric salts for the synthesis of chiral pyridoindole based building block.In the study of chiral acid selectivity of poly(3,4-ethylenedioxythiophene) (PEDOT) based chiral conducting?polymers.

Technology Process of (r)-Mandelic acid

There total 415 articles about (r)-Mandelic 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: 75.0%

[bis(acetoxy)iodo]benzene (3240-34-4) + Ethyl 2-phenylethanoate (101-97-3) → MANDELIC ACID (611-71-2,611-72-3,17199-29-0,90-64-2)

Guidance literature:

With potassium hydroxide; In water; benzene;

DOI:10.1016/S0040-4039(01)90541-6

Reference yield: 75.0%

C17H18N2O5S (85515-89-5) → MANDELIC ACID (611-71-2,611-72-3,17199-29-0,90-64-2)

Guidance literature:

With copper dichloride; In methanol; water; for 20h; Heating;

Reference yield: 50.0%

[bis(acetoxy)iodo]benzene (3240-34-4) + benzeneacetic acid methyl ester (101-41-7) → MANDELIC ACID (611-71-2,611-72-3,17199-29-0,90-64-2)

Guidance literature:

With potassium hydroxide; In water; benzene;

DOI:10.1016/S0040-4039(01)90541-6

upstream raw materials:

2-(morpholin-4-yl)ethanethiol

2,2-dihydroxy-1-phenyl-ethanone

tetrachloromethane

1-Phenyl-2-propen-1-ol

Downstream raw materials:

mandelic acid-tetrahydrofurfuryl ester

N-(5-chloro-[2]pyridyl)-mandelamide

N-(5-bromo-[2]pyridyl)-mandelamide

benzyl 2-hydroxy-2-phenylacetate

Refernces

• 1、 Tarhan, Tuba,Tural, Bilsen,Tural, Servet,Topal, Giray. "Enantioseparation of Mandelic Acid Enantiomers with Magnetic Nano-Sorbent Modified by a Chiral Selector". . p. 835 - 842. Retrieved 2015.
• 2、 Yao, Changjin,Cao, Yan,Wu, Shanshan,Li, Shuang,He, Bingfang. "An organic solvent and thermally stable lipase from Burkholderia ambifaria YCJ01: Purification, characteristics and application for chiral resolution of mandelic acid". . p. 105 - 110. Retrieved 2013.
• 3、 Zhang, Xin-Hong,Liu, Zhi-Qiang,Xue, Ya-Ping,Yang, Bo,Xu, Ming,Zheng, Yu-Guo. "R-mandelic acid production with immobilized recombinant Escherichia coli cells in a recirculating packed bed reactor". . p. 205 - 211. Retrieved 2016.
• 4、 Kaul, Praveen,Banerjee, Anirban,Mayilraj,Banerjee, Uttam C.. "Screening for enantioselective nitrilases: Kinetic resolution of racemic mandelonitrile to (R)-(-)-mandelic acid by new bacterial isolates". . p. 207 - 211. Retrieved 2004.
• 5、 Woehler. "-". . p. 240. Retrieved 1848.
• 6、 Zhang, Yan,Mao, Shimin,Ray, Ajay K.,Rohani, Sohrab. "Nucleation and growth kinetics of (R)-mandelic acid from aqueous solution in the presence of the opposite enantiomer". . p. 2879 - 2887. Retrieved 2010.
• 7、 Liu, Zhi-Qiang,Zhang, Xin-Hong,Xue, Ya-Ping,Xu, Ming,Zheng, Yu-Guo. "Improvement of alcaligenes faecalis nitrilase by gene site saturation mutagenesis and its application in stereospecific biosynthesis of (R)-(-)-mandelic acid". . p. 4685 - 4694. Retrieved 2014.
• 8、 Marckwald,Mc Kenzie. "-". . . Retrieved 1901.
• 9、 -. "High-yield DL-mandelic acid synthesis process". . . Retrieved 2021/09/04.
• 10、 Singh, Kishanpal,Sohal, Harvinder Singh,Singh, Baljit. "Synthesis of α-hydroxycarboxylic acids from various aldehydes and ketones by direct electrocarboxylation: A facile, efficient and atom economy protocol". . p. 839 - 845. Retrieved 2021/04/09.