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D-mandelic acid

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Name

D-mandelic acid

EINECS 210-276-6
CAS No. 611-71-2 Density 1.321 g/cm3
PSA 57.53000 LogP 0.80460
Solubility It is partly soluble in water, freely soluble in isopropyl and ethyl alcohol. Melting Point 131-133 °C(lit.)
Formula C8H8O3 Boiling Point 321.8 °C at 760 mmHg
Molecular Weight 152.15 Flash Point 162.6 °C
Transport Information N/A Appearance white to light yellow crystal powder
Safety 22-24/25-36-26 Risk Codes 41-36/37/38
Molecular Structure Molecular Structure of 611-71-2 (Mandelic acid) Hazard Symbols IrritantXi
Synonyms

Benzeneaceticacid, a-hydroxy-, (R)-;Mandelic acid, D-(8CI);(-)-(R)-Mandelic acid;(-)-D-Mandelic acid;(-)-Mandelic acid;(-)-a-Hydroxyphenylacetic acid;(R)-(-)-Hydroxyphenylaceticacid;(R)-(-)-Mandelic acid;(R)-2-Hydroxy-2-(phenyl)ethanoic acid;(R)-2-Hydroxy-2-phenylacetic acid;(R)-Hydroxy(phenyl)acetic acid;(R)-Mandelicacid;(R)-Mandelic acid;(R)-a-Hydroxybenzeneaceticacid;(R)-a-Hydroxyphenylacetic acid;D(-)-Mandelic acid;D-2-Phenylglycolic acid;D-Mandelic acid;R-(-)-Mandelic acid;Mandelic acid;

Article Data 453

D-mandelic acid Synthetic route

532-28-5, 613-88-7

(RS)-mandelonitrile

611-71-2

(R)-Mandelic Acid

Conditions
ConditionsYield
In aq. phosphate buffer at 40℃; for 0.5h; pH=8; Reagent/catalyst; Time;100%
With Escherichia coli M15/BCJ2315 harboring the nitrilase BCJ2315 from Burkholderia cenocepacia J2315 wet cells In methanol; aq. phosphate buffer for 24h; pH=8; Large scale; enantioselective reaction;93%
With phosphate buffer; nitrilase I In methanol at 37℃; for 3h; pH=8;86%

(2R,5R)-2,5-diphenyloxazolidin-4-one

611-71-2

(R)-Mandelic Acid

Conditions
ConditionsYield
With hydrogenchloride In water-d2 at 100℃; for 16h; Inert atmosphere;100%
1578-63-8

d'acide 2-fluoro-2-phenyl acetique

A

611-71-2

(R)-Mandelic Acid

B

63818-94-0

(R)-α-fluoro-α-phenylacetic acid

Conditions
ConditionsYield
With fluoroacetate dehalogenase RPA1163-W185N for 1h; Catalytic behavior; Kinetics; Enzymatic reaction; enantioselective reaction;A 96.4%
B 96.7%
With fluoroacetate dehalogenase RPA1163 In aq. buffer at 30℃; for 2h; pH=7.5; Kinetics; Catalytic behavior; Resolution of racemate; Microbiological reaction; Enzymatic reaction; enantioselective reaction;A n/a
B n/a
16355-00-3

(R)-1-phenyl-1,2-ethanediol

611-71-2

(R)-Mandelic Acid

Conditions
ConditionsYield
With sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; potassium bromide In acetone at 0℃; pH=8.3; chemoselective reaction;96%
With recombinant alditol oxidase from Streptomyces coelicolor A3(2); catalase from bovine liver at 25℃; pH=7.5; Kinetics; Reagent/catalyst; Temperature; pH-value; aq. phosphate buffer; Enzymatic reaction; enantioselective reaction;
102061-02-9

(S)-2-hydroxymethyl-N-((R)-2-hydroxy-2-phenyl)-acetyl pyrrolidine

611-71-2

(R)-Mandelic Acid

Conditions
ConditionsYield
With sulfuric acid In water at 90℃; for 0.5h;95%
With sulfuric acid at 90℃; for 0.5h;93%
611-73-4

Benzoylformic acid

611-71-2

(R)-Mandelic Acid

Conditions
ConditionsYield
With C48H50N2O2P2Ru*2C18H15P*4Cl(1-)*2Ru(2+); hydrogen; sodium acetate; triphenylphosphine In methanol at 0℃; under 30003 Torr; for 24h; Autoclave; enantioselective reaction;94%
With phosphate buffer; D-glucose; 2-hydroxyethanethiol; sodium chloride; 1,4-dihydronicotinamide adenine dinucleotide; benzoylformate reductase In water; toluene at 30℃; for 48h; Product distribution; Other catalysts: bovine serum albumin, yeast alcohol dehydrogenase, glucose dehydrogenase, formate dehydrogenase;93%
With phosphate buffer; D-glucose; 2-hydroxyethanethiol; sodium chloride; formate dehydrogenase; 1,4-dihydronicotinamide adenine dinucleotide; benzoylformate reductase; bovine serum albumin; yeast alcohol dehydrogenase In ethanol; water; toluene at 30℃; for 48h;93%
882409-00-9

(1S,2S)-trans-2-(N-benzyl)amino-1-cyclohexanol (S)-mandelic acid salt

A

611-71-2

(R)-Mandelic Acid

B

(1S,2S)-2-trans-2-(benzylamino)cyclohexanol hydrochloride

Conditions
ConditionsYield
With hydrogenchloride In water; ethyl acetateA 94%
B n/a
108-05-4

vinyl acetate

A

611-71-2

(R)-Mandelic Acid

B

7322-88-5

(S)-acetylmandelic acid

Conditions
ConditionsYield
In acetone; toluene at 37℃; for 24h; Pseudomonas sp. lipase;A 92%
B 84%
With Burkholderia ambifaria YCJ01 lipase In di-isopropyl ether at 50℃; for 26h; Resolution of racemate; Enzymatic reaction; enantioselective reaction;A n/a
B n/a
With lipase LC2-8 from P. stutzeri LC2-8 In di-isopropyl ether at 30℃; Solvent; Temperature; Resolution of racemate; Enzymatic reaction;A n/a
B n/a

L-1-(1-pyrrolidinyl)-1-propanone-D-(-)-mandelic acid

A

19134-50-0

(SR)-(+/-)-1-phenyl-2-(1-pyrrolidinyl)-1-propanone

B

611-71-2

(R)-Mandelic Acid

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide In water; ethyl acetate at 0 - 80℃; for 5h; pH=2;A 89.2%
B n/a

C22H18O4

611-71-2

(R)-Mandelic Acid

Conditions
ConditionsYield
With potassium phosphate; tris(2,2-bipyridine)ruthenium(II) hexafluorophosphate; ascorbic acid In water; acetonitrile at 20℃; for 1h; Irradiation;89%

D-mandelic acid Specification

The D-mandelic acid is an organic compound with the formula C8H8O3. The IUPAC name of this chemical is (2R)-2-hydroxy-2-phenylacetic acid. With the CAS registry number 611-71-2, it is also named as 2-hydroxy-2-phenylacetic acid. The product's categories are Fine Chemical & Intermediates; Chiral Compounds; Chiral; Miscellaneous; Analytical Chemistry; Carboxylic Acids (Chiral); Chiral Building Blocks; e.e. / Absolute Configuration Determination (NMR); Enantiomer Excess & Absolute Configuration Determination; for Resolution of Bases; Optical Resolution; Synthetic Organic Chemistry; Chiral Compound. Besides, it is a white to light yellow crystal powder, which should be stored in a closed cool and dry place.

Physical properties about D-mandelic acid are: (1)ACD/LogP: 0.55; (2)ACD/LogD (pH 5.5): -1.98; (3)ACD/LogD (pH 7.4): -3.12; (4)ACD/BCF (pH 5.5): 1.00; (5)ACD/BCF (pH 7.4): 1.00; (6)ACD/KOC (pH 5.5): 1.00; (7)ACD/KOC (pH 7.4): 1.00; (8)#H bond acceptors: 3 ; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 3; (11)Index of Refraction: 1.591; (12)Molar Refractivity: 38.904 cm3; (13)Molar Volume: 115.131 cm3; (14)Polarizability: 15.423 10-24cm3; (15)Surface Tension: 60.4739990234375 dyne/cm; (16)Density: 1.322 g/cm3; (17)Flash Point: 162.649 °C; (18)Enthalpy of Vaporization: 59.501 kJ/mol; (19)Boiling Point: 321.827 °C at 760 mmHg

Preparation of D-mandelic acid: this chemical can be prepared by 2,2-dichloro-1-phenyl-ethanone. This reaction will need reagent NaOH-solution.



Uses of D-mandelic acid: it can be used to produce acetoxy-phenyl-acetic acid bt heating. This reaction time is 1 hour.

When you are using this chemical, please be cautious about it as the following:
It is risk of serious damage to eyes. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. Besides, this chemical is irritating to eyes, respiratory system and skin. When you are using it, wear suitable protective clothing, do not breathe dust and avoid contact with skin and eyes.

You can still convert the following datas into molecular structure:
(1)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;
(2)InChIKey=IWYDHOAUDWTVEP-SSDOTTSWSA-N;
(3)Smilesc1([C@H](C(O)=O)O)ccccc1

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