3D Mol Similar

(S)-(+)-Mandelic acid

Iupac Name：(2S)-2-hydroxy-2-phenylacetic acid

CAS No.: 17199-29-0

Molecular Weight：152.15

Modify Date.: 2022-11-25 02:19

Introduction:

Solid

(S)-mandelic acid is a (2S)-2-hydroxy monocarboxylic acid and a mandelic acid. It is a conjugate acid of a (S)-mandelate. It is an enantiomer of a (R)-mandelic acid.

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1. Names and Identifiers

1.1 Name: (S)-(+)-Mandelic acid
1.2 Synonyms: (+)-(S)-Mandelic acid (+)-L-MANDELIC ACID (+)-Mandelic acid (+)-α-Hydroxyphenylacetic acid (2S)-2-Hydroxy-2-(phenyl)ethanoic acid (2S)-2-Hydroxy-2-phenylacetic acid (2S)-Hydroxy(phenyl)acetic acid (2S)-hydroxy(phenyl)ethanoic acid (S)-(+)-2-hydroxy-2-phenylacetic acid (S)-(+)-alpha-Hydroxyphenylacetic acid (S)-(+)-Amygdalic Acid (S)-(+)-Hydroxyphenylacetic acid (s)-(+)-mandelic (S)-2-Hydroxy-2-(phenyl)ethanoic acid (S)-2-Hydroxy-2-phenylacetic acid (S)-Amygdalic acid (s)-benzeneaceticaci (S)-Hydroxyphenylaceticacid (S)-Mandelate (S)-Mandelic acid (S)-α-Hydroxybenzeneacetic acid (S)-α-Hydroxyphenylacetic acid (αS)-α-Hydroxybenzeneacetic acid 2-phenyl-2-hydroxyethanoic acid Benzeneacetic acid, α-hydroxy-, (S)- Benzeneacetic acid, α-hydroxy-, (αS)- Benzeneaceticacid,alpha-hydroxy-,(S)- EINECS 241-240-8 hydroxyphenylacetic acid L-(+)-Mandelic acid L-(+)-α-Hydroxybenzeneacetic acid L-mandelate L-Mandelic acid Mandelic acid, L-(+)- MFCD00004495 phenyl-hydroxy-acetic acid S-(+)-Mandelic acid S-mandelic acid

1.3 CAS No.: 17199-29-0

1.4 CID: 439616

1.5 EINECS(EC#): 241-240-8

1.6 Molecular Formula: C8H8O3 (isomer)

1.7 Inchi: 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

1.8 InChkey: IWYDHOAUDWTVEP-ZETCQYMHSA-N

1.9 Canonical Smiles: C1=CC=C(C=C1)C(C(=O)O)O

1.10 Isomers Smiles: C1=CC=C(C=C1)[C@@H](C(=O)O)O

2. Properties

2.1 Density: 1.3410

2.1 Melting point: 131-134 °C(lit.)

2.1 Boiling point: 234.6°C (rough estimate)

2.1 Refractive index: 153.5 ° (C=1, H2O)

2.1 Flash Point: 162.6°C

2.1 Precise Quality: 152.04700

2.1 PSA: 57.53000

2.1 logP: 0.80460

2.1 Solubility: 100 g/L (25 ºC)

2.2 Appearance: White crystals

2.3 Storage: Light Sensitive. Ambient temperatures.

2.4 Chemical Properties: white to light yellow crystal powde

2.5 Color/Form: White to Yellow Solid

2.6 PH: 2.1 (60g/l, H2O, 20℃)

2.7 Physical: Solid

2.8 pKa: 3.41±0.25(Predicted)

2.9 Water Solubility: H2O: 100 g/L (25 oC)

2.10 Stability: Stable, but light sensitive. Combustible. Incompatible with strong bases, strong oxidizing agents, strong reducing agents.

2.11 StorageTemp: Store below +30°C.

3. Use and Manufacturing

3.1 GHS Classification: Signal: Danger
GHS Hazard Statements
Aggregated GHS information provided by 144 companies from 16 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria by 9 of 144 companies. For more detailed information, please visit ECHA C&L website

Of the 15 notification(s) provided by 135 of 144 companies with hazard statement code(s):

H302 (34.81%): Harmful if swallowed [Warning Acute toxicity, oral]
H315 (45.19%): Causes skin irritation [Warning Skin corrosion/irritation]
H318 (91.11%): Causes serious eye damage [Danger Serious eye damage/eye irritation]
H335 (44.44%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P310, P312, P321, P330, P332+P313, P362, P403+P233, P405, and P501

3.2 Purification Methods: Purify the mandelic acids by recrystallisation from H2O, *C6H6 or CHCl3. [Roger J Chem Soc 2168 1932,Jamison & Turner J Chem Soc 611 1942.] They have solubilities in H2O of ca 11% at 25o. [Banks & Davies J Chem Soc 73 1938.] The S-benzylisothiuronium salts has m 180o (from H2O) and [] D 25 (+) and (-) 57o (c20, EtOH) [El Masri et al. Biochem J 68 199 1958]. [Beilstein 10 IV 564.] (S)-(+)-Mandelic acid Preparation Products And Raw materials Preparation Products

3.3 Usage: Antiseptic (urinary).

4. Safety and Handling

4.1 Hazard Codes: Xi

4.1 Risk Statements: 36/37/38

4.1 Safety Statements: 22-24/25-37/39-26-36

4.1 Hazard Declaration: H302

4.1 RIDADR: 25kgs in

4.1 Caution Statement: P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P310, P312, P321, P330, P332+P313, P362, P403+P233, P405, P501

4.1 WGK Germany: 3

4.1 Sensitive: Light Sensitive

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Serious eye damage, Category 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H318 Causes serious eye damage
Precautionary statement(s)
Prevention	P280 Wear protective gloves/protective clothing/eye protection/face protection.
Response	P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P310 Immediately call a POISON CENTER/doctor/\u2026
Storage	none
Disposal	none

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

Mass spectrum (electron ionization)

7. Synthesis Route

17199-29-0Total: 5 Synthesis Route

93-56-1 55 Suppliers

17199-29-0 294 Suppliers

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611-73-4 87 Suppliers

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Literatures:
Bioscience, Biotechnology, and Biochemistry, , vol. 56, # 8 p. 1216 - 1220
Yield: null

611-71-2 321 Suppliers

17199-29-0 294 Suppliers

611-71-2 321 Suppliers

611-73-4 87 Suppliers

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Literatures:
Huang, Han-Rong; Xu, Jian-He; Xu, Yi; Pan, Jiang; Liu, Xiang Tetrahedron Asymmetry, 2005 , vol. 16, # 12 p. 2113 - 2117
Yield: ~1%

4067-91-8

17199-29-0 294 Suppliers

3886-69-9 267 Suppliers

Literatures:
Zingg, S. P.; Arnett, Edward M.; McPhail, Andrew T.; Bothner-By, Aksel A.; Gilkerson, W. R. Journal of the American Chemical Society, 1988 , vol. 110, # 5 p. 1565 - 1580
Yield: null

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8. Other Information

8.0 Dissociation Constants: 3.41 (at 25 °C)

8.1 Collision Cross Section: 130.6 ?2 [M-H]-

8.2 Manufacturing Info: Benzeneacetic acid, .alpha.-hydroxy-, (.alpha.S)-: ACTIVE

8.3 BRN: 2208678

8.4 Chemical Properties: white to light yellow crystal powde

8.5 Uses: Antiseptic (urinary).

8.6 Purification Methods: Purify the mandelic acids by recrystallisation from H2O, *C6H6 or CHCl3. [Roger J Chem Soc 2168 1932,Jamison & Turner J Chem Soc 611 1942.] They have solubilities in H2O of ca 11% at 25o. [Banks & Davies J Chem Soc 73 1938.] The S-benzylisothiuronium salts has m 180o (from H2O) and [] D 25 (+) and (-) 57o (c20, EtOH) [El Masri et al. Biochem J 68 199 1958]. [Beilstein 10 IV 564.]

8.7 Usage: (S)-(+)-Mandelic acid is a versatile reagent used in the resolution of racemates and the preparation of amides, Pharmaceutical Intermediates.

8.8 Uses: A versatile reagent used in the resolution of racemates and the preparation of amides.

8.9 Purification Methods: Purify the mandelic acids by recrystallisation from H2O, *C6H6 or CHCl3. [Roger J Chem Soc 2168 1932,Jamison & Turner J Chem Soc 611 1942.] They have solubilities in H2O of ca 11% at 25o. [Banks & Davies J Chem Soc 73 1938.] The S-benzylisothiuronium salts has m 180o (from H2O) and [] D 25 (+) and (-) 57o (c20, EtOH) [El Masri et al. Biochem J 68 199 1958]. [Beilstein 10 IV 564.]

9. Computational chemical data

Molecular Weight: 152.15g/mol
Molecular Formula: C₈H₈O₃
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 152.047344113
Monoisotopic Mass: 152.047344113
Complexity: 138
Rotatable Bond Count: 2
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 3
Topological Polar Surface Area: 57.5
Heavy Atom Count: 11
Defined Atom Stereocenter Count: 1
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADccBwMAAAAAAAAAAAAAAAAAAAAAAAAAAwAAAAAAAAAAABAAAAGgAACAAADBSgmAIwCIAAAgCIAiDSCAICAAAgAAAIiAFACIgJNjKAFRCAcAAkwAEJmAeIyKCOAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

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