24256-91-5

Basic information

• Product Name: (S)-2-Hydroxy-2-phenylbutyric acid
• Synonyms: (S)-2-Hydroxy-2-phenylbutyric acid;(+)-α-Ethyl-L-mandelic acid;(S)-2-Phenyl-2-hydroxybutanoic acid;[S,(+)]-α-Ethyl-α-hydroxybenzeneacetic acid
• CAS NO: 24256-91-5
• Molecular Formula: C₁₀H₁₂O₃
• Molecular Weight: 180.2
• Product Categories: Carboxylic Acids;Chiral Building Blocks;Organic Building Blocks
• Mol File: 24256-91-5.mol
• Article Data: 13

Chemical Properties

• Melting Point: 110-116 °C
• Appearance: /
• CAS DataBase Reference: (S)-2-Hydroxy-2-phenylbutyric acid(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-2-Hydroxy-2-phenylbutyric acid(24256-91-5)
• EPA Substance Registry System: (S)-2-Hydroxy-2-phenylbutyric acid(24256-91-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26
• Hazardous Substances Data: 24256-91-5(Hazardous Substances Data)

Usage

General Description

(S)-2-Hydroxy-2-phenylbutyric acid, also known as mandelic acid, is a chiral aromatic alpha hydroxy acid. It is commonly used in skincare products due to its exfoliating properties, which help to remove dead skin cells and promote a more even skin tone. Mandelic acid is also known for its antibacterial and anti-inflammatory properties, making it effective in treating acne and other skin conditions. In addition, it has been studied for its potential use in the treatment of hyperpigmentation and anti-aging effects. Overall, (S)-2-Hydroxy-2-phenylbutyric acid has a variety of skincare benefits and is commonly used in cosmetic formulations.

Upstream product

• 1603-79-8 phenylglyoxylic acid ethyl ester 
• 925-90-6 ethylmagnesium bromide 
• 77207-58-0 (S)-(+)-5-ethyl-5-phenyl-2,4-oxazolidinedione 
• 89616-49-9 (R)-2-hydroxy-2-phenyl-butyric acid methyl ester 
• 69489-15-2 (S)-(-)-hydroxy-2-phenylbutanal 
• 1258406-59-5 2-(2-chlorophenyl)-5-ethyl-5-phenyl-3-tosyloxazolidin-4-one 
• 115156-59-7 (S)-1-((2S,4aS,7R,8aR)-3-Benzyl-4,4,7-trimethyl-octahydro-benzo[e][1,3]oxazin-2-yl)-1-phenyl-propan-1-ol 
• 115156-57-5 (2S,4aS,7R,8aR)-2-benzoyl-N-benzyl-4,4,7-trimethyl-octahydro-1,3-benzoxazine 
• 1074-12-0 phenylglyoxal hydrate 
• 20229-41-8 l-menthyl phenylglyoxylate 
• 611-73-4 Benzoylformic acid 
• 141652-48-4 <(1R,2R)-2-phenoxycyclohex-1-yl> phenylglyoxalate 
• 89616-54-6 (R)-1-Phenyl-1-((2S,4aR,7R,8aS)-4,4,7-trimethyl-hexahydro-1-oxa-3-thia-naphthalen-2-yl)-propan-1-ol 
• 89616-56-8 Phenyl-((2S,4aR,7R,8aS)-4,4,7-trimethyl-hexahydro-1-oxa-3-thia-naphthalen-2-yl)-methanone 

Downstream Products

• 27739-61-3 (S)-2-hydroxy-1,2-diphenyl-butanone-⁽¹⁾ 
• 144786-54-9 (S)-2-hydroxy-2-phenylbutanamide 
• 5180-33-6 1,1-Diphenyl-propan-1-ol 
• 114489-01-9 9-O-<(S)-2-hydroxy-2-phenylbutyryl>heliotridine 
• 114422-98-9 7-O-<(S)-2-hydroxy-2-phenylbutyryl>heliotridine 
• 114422-99-0 7,9-di-O-<(S)-2-hydroxy-2-phenylbutyryl>heliotridine 
• 114489-05-3 (S)-2-Hydroxy-2-phenyl-butyric acid (1S,7aR)-7-((R)-2-hydroxy-2-phenyl-butyryloxymethyl)-2,3,5,7a-tetrahydro-1H-pyrrolizin-1-yl ester 
• 81340-08-1 9-O-<(S)-(+)-2-hydroxy-2-phenylbutyryl>retronecine 
• 13448-81-2 (S)-methyl atrolactate 
• 76496-47-4 (S)-2-hydroxy-2-phenyl-butyric acid methyl ester 

Relevant articles and documents

HAUTS RENDEMENTS OPTIQUES OBTENUS DANS LA SYNTHESE D'α-ALKYLα-HYDROXYESTERS PAR REACTION D'ALKOXYTRIALKYLALUMINATES ENCOMBRES AVEC LE PHENYLGLYOXALATE DE MENTHYLE.

Enantiomeric purities in alkylation of (+) and (-) menthyl esters of phenylglyoxilic acid by complexes derived from AlEt3 and the lithium salts of (+) and racemic Darvon alcohol are depending upon the only stereochemistry of the menthyl group in ester.These results suggest that the observed stereochemistry is to be related to the bulkiness of the organometallic reagent, which overcomes the asymetric induction due to the chiral center of the alkoxy moiety.Accordingly, use of complexes from AlEt3 and non chiral alcohols of increasing sizes leads to increasing stereoselectivity.

Formal [3+2]-cycloaddition of ketenes and oxaziridines catalyzed by chiral lewis bases: Enantioselective synthesis of oxazolin-4-ones

Choose the right cat.: A highly enantioselective synthesis of oxazolin-4-ones by the formal [3+2]-cycloaddition of ketenes and a racemic oxaziridines has been developed (see scheme; cat.=N-heterocyclic carbenes for disubstituted ketenes or cinchona alkaloids for monosubstituted ketenes, Ts=4-toluenesulfonyl).

Isomannide and isosorbide as new chiral auxiliaries for the stereoselective synthesis of tertiary α-hydroxy acids

Isomannide and isosorbide are selectively protected to provide new chiral auxiliaries suitable for the preparation of enantiopure tertiary α-hydroxy acids. Diastereoselective additions of organozinc reagents on the derived phenylglyoxylates afford the desired α-hydroxy acids with 60-99% ee after saponification. Both absolute configurations of the α-hydroxy acids can be accessed, by adapted choice of either the starting diol or the protecting group.

New cyclohexyl-based chiral auxiliaries: Enantioselective synthesis of α-hydroxy acids

(1R,2R)-2-(4-tert-butylphenoxy) cyclohexan-1-ol (5) and (1R,2R)-2-(4-phenylphenoxy) cyclohexan-1-ol (6) have been used for the first time as chiral auxiliaries. Addition of alkylzinc chlorides to the corresponding glyoxylates 5a, 6a, after hydrolysis, provided (R)-α-hydroxy acids in high optical purities.