(R)-(-)-Mandelic acid - 10mM in DMSO , CAS No.611-71-2

CAS: 611-71-2 Cat. No.: R425065 Molecular Weight: 152.15 Beilstein Registry Number: 2691094 EC Number: 210-276-6

GRADE & PURITY 10mM in DMSO

Synonyms

(-)-Mandelic acid | mandelic_acid | s9003 | 1mcz | D-(-)-Mandelic acid, puriss., >=99.0% (T) | NCGC00166022-01 | (-)-(R)-Mandelate | D70151 | (-)-(R) alpha-hydroxybenzeneacetic acid | DTXSID4046523 | SR-01000946767-1 | (-)-alpha-Hydroxyphenylacetic acid |

Storage

Protected from light,Store at -80°C

Shipped In

Dry ice packs + Cold packs

Overview

(R)-(-)-Mandelic acid, a chiral resolving agent, is also used as a building block to synthesize pharmaceutical drugs such as penicillin and cephalosporin. It can be synthesized from (R,S)-mandelonitrile with high yield and enantioselectivity using nitrilase enzyme.
R-(-)-Mandelic Acid is a synthetic intermediate commonly used for pharmaceutical synthesis. ;(R)-(-)-Mandelic acid has been used in studies to assess its ability to undergo spontaneous oscillatory chiral conversion and spontaneous condensation to form polymandelic acid.

Specifications

Synonyms

(-)-Mandelic acid | mandelic_acid | s9003 | 1mcz | D-(-)-Mandelic acid, puriss., >=99.0% (T) | NCGC00166022-01 | (-)-(R)-Mandelate | D70151 | (-)-(R) alpha-hydroxybenzeneacetic acid | DTXSID4046523 | SR-01000946767-1 | (-)-alpha-Hydroxyphenylacetic acid |

Specifications & Purity

10mM in DMSO

Storage

Protected from light, Store at -80°C

Shipped In

Dry ice packs + Cold packs

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

INHIBITOR

Names and Identifiers

• Canonical Smiles: C1=CC=C(C=C1)C(C(=O)O)O
• IUPAC Name: (2R)-2-hydroxy-2-phenylacetic acid
• InChIKey: IWYDHOAUDWTVEP-SSDOTTSWSA-N
• INCHI: 1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)/t7-/m1/s1
• Isomeric SMILES: C1=CC=C(C=C1)[C@H](C(=O)O)O
• WGK Germany: 1
• Molecular Weight: 152.15
• Beilstein: 2691094
• Reaxy-Rn: 510011
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=510011&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Benzene and substituted derivatives
• Alternative Parents: Alpha hydroxy acids and derivatives Secondary alcohols Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds Aromatic alcohols
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Hydroxy acid - Monocyclic benzene moiety - Alpha-hydroxy acid - Secondary alcohol - Monocarboxylic acid or derivatives - Carboxylic acid - Carboxylic acid derivative - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Aromatic alcohol - Organooxygen compound - Carbonyl group - Alcohol - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
• External Descriptors: mandelic acid

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

PTPN7 Tchem Protein-tyrosine phosphatase LC-PTP (886 Activities)

Discover Target: PTPN7

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

GAPDH Tchem Glyceraldehyde-3-phosphate dehydrogenase liver (1284 Activities)

Discover Target: GAPDH

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Ptpn1 Protein-tyrosine phosphatase 1B (270 Activities)

Discover Target: Ptpn1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

mdlA Mandelate racemase (27 Activities)

Discover Target: mdlA

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Dusp6 Dual specificity protein phosphatase 6 (459 Activities)

Discover Target: Dusp6

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

rep Replicase polyprotein 1ab (378 Activities)

Discover Target: rep

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Sensitivity: Light sensitive.
• Specific Rotation[α]: -150.0 to -157.0 deg(C=1, H2O)
• Flash Point(°F): >374 °F
• Flash Point(°C): >190 °C
• Melt Point(°C): 131-135°C
• Molecular Weight: 152.150 g/mol
• XLogP3: 0.600
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 152.047 Da
• Monoisotopic Mass: 152.047 Da
• Topological Polar Surface Area: 57.500 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 138.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

References

1. Tiantian Wan, Zulei Zhang, Hailong Wang, Yiwen Yang, Hanxing Yang, Jian Zhang, Yanbo Zeng, Lei Li, Jinchun Li.  (2022)  Rapid and highly selective detection of chlorogenic acid in fruit samples by Fe3O4@SiO2@PIL with boron affinity via a fluorescence enhanced strategy.  NEW JOURNAL OF CHEMISTRY,  47  (2): (828-837).  [PMID:] [10.1039/D2NJ04750K]

2. Qi Shen, Xiao-Ting Zhou, Qian Guo, Yu-Zhen Xue, Ya-Ping Xue, Yu-Guo Zheng.  (2022)  Potential of the Signal Peptide Derived from the PAS_chr3_0030 Gene Product for Secretory Expression of Valuable Enzymes in Pichia pastoris.  APPLIED AND ENVIRONMENTAL MICROBIOLOGY,      [PMID:35435711] [10.1128/aem.00296-22]

3. Xiaohui Niu, Simeng Yan, Jinliang Chen, Hongxia Li, Kunjie Wang.  (2022)  Enantioselective recognition of L/D-amino acids in the chiral nanochannels of a metal-organic framework.  ELECTROCHIMICA ACTA,      [PMID:] [10.1016/j.electacta.2021.139809]

4. Xie Chao, Lin Longfei, Huang Liang, Wang Zixin, Jiang Zhiwei, Zhang Zehui, Han Buxing.  (2021)  Zn-Nx sites on N-doped carbon for aerobic oxidative cleavage and esterification of C(CO)-C bonds.  Nature Communications,  12  (1): (1-12).  [PMID:34376654] [10.1038/s41467-021-25118-0]

5. Mengyun Lu, Xinwen Jia, Wenjing Zhang, Wuduo Zhao, Ajuan Yu, Gangfeng Ouyang.  (2024)  Enhanced Enantioselective Sensing of 1,1′-Bi-2-naphthol and Mandelic Acid by Proportional Fluorescence Sensor 3DOM Zn-MOF-74-l-Trp with Hierarchical Macro–Micropore Structure.  INORGANIC CHEMISTRY,      [PMID:39661170] [10.1021/acs.inorgchem.4c04464]

6. Jinglin Shen, Jing Fu, Paritosh Mahato, Minggan Wang, Baicheng Liu, Zhe Yang, Wei Qi, Di Sun, Xia Xin.  (2025)  Gold Nanocluster Isomerization Drives Supramolecular Transition from Heterochiral to Homochiral Helices.  ACS Nano,      [PMID:40844432] [10.1021/acsnano.5c08207]

7. Detao Li, Zichen Ning, Feiqiang He, Zhi Gao, Limin Zhou, Li Xu, Zhijian Zheng, Jerry Heng, Shichao Du, Jinbo Ouyang.  (2025)  Competitive Chiral Cocrystallization Inspired Enantioseparation: Mechanistic Insights into R/S-Mandelic Acid and d/l-Prolinamide.  CRYSTAL GROWTH & DESIGN,      [PMID:] [10.1021/acs.cgd.5c00692]

8. Qi Duan, Zhicheng Ye, Kangfu Zhou, Feifei Wang, Cheng Lian, Yazhuo Shang, Honglai Liu.  (2024)  An Investigation into the Transdermal Behavior of Active Ingredients by Combination of Experiments and Multiscale Simulations.  JOURNAL OF PHYSICAL CHEMISTRY B,      [PMID:38913878] [10.1021/acs.jpcb.4c00735]

9. Xi-Meng Li, Bei-Ni Chen, Zheng-Quan Nie, Jian-Mei Yang, Jun-Nan He, Tong Yang, Jun-Hui Zhang, Jin-Xin Yang, Lei Zhang, Yan Zhao, Yue Sun, Jin Zhang.  (2025)  A chiral electrochemical sensor for detecting the enantiomeric ratio of mandelic acid and studying the enantioselective mechanism.  MICROCHEMICAL JOURNAL,      [PMID:] [10.1016/j.microc.2025.115840]