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279900

Sigma-Aldrich

(S)-(+)-2-Phenylpropionic acid

97%

Synonym(s):

(S)-(+)-Hydratropic acid, (S)-HTA

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About This Item

Linear Formula:
CH3CH(C6H5)CO2H
CAS Number:
7782-24-3
Molecular Weight:
150.17
Beilstein:
2044507
MDL number:
MFCD00063139
UNSPSC Code:
12352002
PubChem Substance ID:
24856916
NACRES:
NA.22

Quality Level

100

Assay

97%

form

solid

optical activity

[α]20/D +72°, c = 1.6 in chloroform

optical purity

ee: 98% (HPLC)

refractive index

n20/D 1.522 (lit.)

bp

115 °C/1 mmHg (lit.)

mp

29-30 °C (lit.)

density

1.1 g/mL at 25 °C (lit.)

SMILES string

C[C@H](C(O)=O)c1ccccc1

InChI

1S/C9H10O2/c1-7(9(10)11)8-5-3-2-4-6-8/h2-7H,1H3,(H,10,11)/t7-/m0/s1

InChI key

YPGCWEMNNLXISK-ZETCQYMHSA-N

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Application

Chiral building block. Resolving agent

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H317,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

>235.4 °F - closed cup

Flash Point(C)

> 113 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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T Yamaguchi et al.
Drug metabolism and disposition: the biological fate of chemicals, 15(4), 535-539 (1987-07-01)
The contribution of the liver and kidney to the optical isomerization of (R)-(-)-2-phenylpropionic acid (hydratropic acid (HTA] was examined by iv injection of racemic HTA (20 mg/kg) to nephrectomized and bile duct-ligated rats (NEBL-rats), eviscerated rats with nonfunctioning livers (EVIS-rats)
Chunze Li et al.
Chemical research in toxicology, 15(10), 1309-1317 (2002-10-22)
Chemically reactive species formed from the metabolism of carboxylic acid-containing compounds have been proposed as mediators of their toxic side-effects. Two alternative metabolic pathways known to be involved in the generation of reactive acylating metabolites of carboxylic acids are acyl
D Ahmad et al.
Chirality, 6(5), 365-371 (1994-01-01)
The significance of disturbances of lipid metabolism caused by xenobiotic acyl-CoAs as possible causes of peroxisomal proliferation has been studied with the enantiomers of 2-phenylpropionic acid (2-PPA), the (R)-enantiomer of which is converted to the acyl-CoA in rats while its
M Sajewicz et al.
Journal of chromatographic science, 43(10), 542-548 (2006-01-28)
The usefulness of thin-layer chromatography (TLC) as an efficient measuring technique in the studies of oscillatory trans-enantiomerization of profens from the S to the R configuration (and vice versa) during their storage as 70% ethanol solutions is demonstrated in the
M J Thomason et al.
Chirality, 9(3), 254-260 (1997-01-01)
Previous investigations have described the development of nongrowing suspensions of Verticillium lecanii as a microbial model of the mammalian chiral inversion of the 2-arylpropionic acids (2-APAs). Mechanistic studies in mammals have shown that inversion involves loss of the alpha-methine proton
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