(S)-(+)-Mandelic acid - ≥99% , CAS No.17199-29-0

CAS: 17199-29-0 Cat. No.: M111210 Formula: C₈H₈O₃ Peso molecolare: 152.15 Beilstein Registry Number: 2208678 Numero EC: 241-240-8

GRADE & PURITY ≥99%

Synonyms

Benzeneacetic acid, alpha-hydroxy-, (alphaS)- | L-(+)-Mandelic acid, purum, >=98.0% (T) | (+)-.ALPHA.-HYDROXYPHENYLACETIC ACID | AC-2496 | alpha-hydroxybenzeneacetate | S-(+)-Mandelic acid | (S)-A-HYDROXYPHENYLACETIC ACID | MLS-0090889.0001 | (S)--(+)--ma

Storage

Room temperature

Shipped In

Normal

Specifications

Sinonimi

Benzeneacetic acid, alpha-hydroxy-, (alphaS)- | L-(+)-Mandelic acid, purum, >=98.0% (T) | (+)-.ALPHA.-HYDROXYPHENYLACETIC ACID | AC-2496 | alpha-hydroxybenzeneacetate | S-(+)-Mandelic acid | (S)-A-HYDROXYPHENYLACETIC ACID | MLS-0090889.0001 | (S)--(+)--ma

Specifiche e purezza

≥99%

Condizioni di conservazione di stoccaggio

Room temperature

Spedito in

Normal

Purezza

≥99%

Nomi e identificatori

• Pubchem Sid: 504758715
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504758715
• Sorrisi canonici: C1=CC=C(C=C1)C(C(=O)O)O
• IUPAC Name: (2S)-2-hydroxy-2-phenylacetic acid
• InChIKey: IWYDHOAUDWTVEP-ZETCQYMHSA-N
• INCHI: 1S/C8H8O3/c9-7(8(10)11)6-4-2-1-3-5-6/h1-5,7,9H,(H,10,11)/t7-/m0/s1
• Isomeri SMILES: C1=CC=C(C=C1)[C@@H](C(=O)O)O
• WGK Germania: 3
• Peso molecolare: 152.15
• Beilstein: 2208678
• 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
    • Classe Benzene and substituted derivatives

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Classe: 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
• Descrizione: 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

Obiettivi associati (umani)

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

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XIAP Tchem Inhibitor of apoptosis protein 3 (3673 Activities)

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SMAD3 Tchem Mothers against decapentaplegic homolog 3 (68039 Activities)

Discover Target: SMAD3

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IDH1 Tclin Isocitrate dehydrogenase [NADP] cytoplasmic (40980 Activities)

Discover Target: IDH1

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Obiettivi associati (non umani)

ampC Beta-lactamase AmpC (62480 Activities)

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Ptpn1 Protein-tyrosine phosphatase 1B (270 Activities)

Discover Target: Ptpn1

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mdlA Mandelate racemase (27 Activities)

Discover Target: mdlA

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Dusp6 Dual specificity protein phosphatase 6 (459 Activities)

Discover Target: Dusp6

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Meccanismi d'azione

Proprietà chimiche e fisiche

• Solubilità: Solubility in Methanol almost transparency
• Sensibilità: Light sensitive
• Rotazione specifica [α]: +150.0 to +157.0 deg(C=1, H2O)
• Punto di infiammabilità (°F): 374.0 °F
• Punto di infiammabilità (°C): > 190 °C
• Punto di fusione (°C): 130-135°C
• Peso molecolare: 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

Riferimenti

1. Li Yuchen, Xu Guangfu, Chen Jiaquan, Yu Tao, Miao Pandeng, Du Yingxiang.  (2023)  One-step synthesis of chiral molecularly imprinted polymer TiO2 nanoparticles for enantioseparation of phenylalanine in coated capillary electrochromatography.  MICROCHIMICA ACTA,  190  (7): (1-11).  [PMID:37391671] [10.1007/s00604-023-05854-4]

2. Niu Xiaohui, Zhao Rui, Yan Simeng, Li Hongxia, Yang Jing, Cao Kunjie, Liu Xiaoyu, Wang Kunjie.  (2023)  Chiral MOFs encapsulated by polymers with poly-metallic coordination as chiral biosensors.  MICROCHIMICA ACTA,  190  (6): (1-12).  [PMID:37208529] [10.1007/s00604-023-05807-x]

3. Liu Nijuan, Liu Jingjing, Niu Xiaohui, Wang Jia, Guo Ruibin, Mo Zunli.  (2021)  An electrochemical chiral sensor based on the synergy of chiral ionic liquid and 3D-NGMWCNT for tryptophan enantioselective recognition.  MICROCHIMICA ACTA,  188  (5): (1-13).  [PMID:33839948] [10.1007/s00604-021-04818-w]

4. Jia Wang, Zunli Mo, Nijuan Liu, Ruibin Guo, Chao Shuai, Fang Chen, Yongxin Du, Jingjing Liu, Guigui Liu, Qibing Dong, Qinqin Gao, Ying Chen, Wentong Liu.  (2021)  Construction of electrochemical chiral interface of C3N4/Ppy/ self-assembled polysaccharide.  JOURNAL OF ELECTROANALYTICAL CHEMISTRY,      [PMID:] [10.1016/j.jelechem.2021.115118]

5. Xiaofei Ma, Yingxiang Du, Xinqi Zhu, Jiangxia Yang.  (2020)  Visual chiral recognition of aromatic amino acids with (S)-mandelic acid-based ionic liquids via complexation.  TALANTA,      [PMID:32498868] [10.1016/j.talanta.2020.121083]

6. Jianjian Zhao, Yaqing Liu, Aiyou Hao, Pengyao Xing.  (2020)  High-Throughput Synthesis of Chiroptical Nanostructures from Synergistic Hydrogen-Bonded Coassemblies.  ACS Nano,      [PMID:32040311] [10.1021/acsnano.0c00352]

7. Zi-Meng Wang, Cheng-Xiong Yang, Xiu-Ping Yan.  (2019)  Polysiloxane assisted fabrication of chiral crystal sponge coated capillary column for chiral gas chromatographic separation.  JOURNAL OF CHROMATOGRAPHY A,      [PMID:31405571] [10.1016/j.chroma.2019.460420]

8. Cun-Duo Tang, Peng-Ju Ding, Hong-Ling Shi, Yuan-yuan Jia, Mao-zhi Zhou, Hui-lei Yu, Jian-He Xu, Lun-Guang Yao, Yun-Chao Kan.  (2019)  One-Pot Synthesis of Phenylglyoxylic Acid from Racemic Mandelic Acids via Cascade Biocatalysis.  JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,      [PMID:30807132] [10.1021/acs.jafc.8b07295]

9. Datong Wu, Wensheng Tan, Yin Yu, Baozhu Yang, Hongda Li, Yong Kong.  (2018)  A facile avenue to prepare chiral graphene sheets as electrode modification for electrochemical enantiorecognition.  ANALYTICA CHIMICA ACTA,      [PMID:30172332] [10.1016/j.aca.2018.06.029]

10. Cun-Duo Tang, Hong-Ling Shi, Jian-He Xu, Zhu-Jin Jiao, Fei Liu, Peng-Ju Ding, Hong-Fei Shi, Lun-Guang Yao, Yun-Chao Kan.  (2018)  Biosynthesis of Phenylglyoxylic Acid by LhDMDH, a Novel d-Mandelate Dehydrogenase with High Catalytic Activity.  JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY,      [PMID:29460618] [10.1021/acs.jafc.7b05835]

11. Zhang Yanjie, Du Shuaijing, Feng Zijie, Du Yingxiang, Yan Zhi.  (2016)  Evaluation of synergistic enantioseparation systems with chiral spirocyclic ionic liquids as additives by capillary electrophoresis.  ANALYTICAL AND BIOANALYTICAL CHEMISTRY,  408  (10): (2543-2555).  [PMID:26894758] [10.1007/s00216-016-9356-8]

12. Zhou Long, Jia Jia, Shanling Wang, Lu Kou, Xiandeng Hou, Michael J. Sepaniak.  (2013)  Visual enantioselective probe based on metal organic framework incorporating quantum dots.  MICROCHEMICAL JOURNAL,      [PMID:] [10.1016/j.microc.2013.08.013]

13. Fangqin Wang, Wenrong Cai, Lilan Tan, Junyao Li, Datong Wu, Yong Kong.  (2024)  A Liquid–Liquid Interfacial Strategy for Construction of Electroactive Chiral Covalent–Organic Frameworks with the Aim to Enlarge the Testing Scope of Chiral Electroanalysis.  ANALYTICAL CHEMISTRY,      [PMID:38335728] [10.1021/acs.analchem.3c05744]

14. Hongmin Zhang, Xiaotong Yang, Xiaona Cui, Hejie Wang, Aixin Song, Xiao Chen, Hong-Guo Liu.  (2024)  Assembly of large-area helical nanowire and nanosphere superstructures by PS-b-P2VP/S-mandelic acid via interfacial nanoarchitectonics.  JOURNAL OF MOLECULAR LIQUIDS,      [PMID:] [10.1016/j.molliq.2024.125020]

15. 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]

16. 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]

17. Qi Zhengfeng, Mao Caiyun, Xu Kai, Zhang Nan, Zhang Wentao, Jiang Ming, Zhang Qinqin, Feng Mi, Xu Fei.  (2026)  Chiral Deep Eutectic Solvents: Hydrogen-Bond Characterization, Physical Properties, and Biomass Dissolution Performance.  JOURNAL OF CHEMICAL AND ENGINEERING DATA,      [PMID:] [10.1021/acs.jced.6c00076]

Domande frequenti

What is the purity of this product?

This product is supplied at ≥99% purity (chemical assay). Lot-specific values are stated on the Certificate of Analysis.

How should this product be stored?

Store at room temperature.

What are the CAS number, molecular formula and molecular weight?

The CAS Number is 17199-29-0, the molecular formula is C8H8O3, and the molecular weight is 152.15 g/mol. InChIKey IWYDHOAUDWTVEP-ZETCQYMHSA-N.

What documentation is provided?

Available product documentation, including Certificates of Analysis (COA), Safety Data Sheets (SDS), and specification sheets, is shown in the product document area. Document availability and access follow the current site policy.

How is this product shipped?

This product ships under standard ambient conditions. No temperature-controlled packaging is required.