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302163

Sigma-Aldrich

(R)-(−)-1-Phenyl-1,2-ethanediol

99%

Synonym(s):

(−)-Styrene glycol, (R)-(−)-Phenylethylene glycol

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About This Item

Linear Formula:
HOCH2CH(C6H5)OH
CAS Number:
Molecular Weight:
138.16
Beilstein:
2355547
MDL number:
UNSPSC Code:
12352002
PubChem Substance ID:
NACRES:
NA.22

Assay

99%

optical activity

[α]20/D −69°, c = 1 in chloroform

bp

272-274 °C (lit.)

mp

64-67 °C (lit.)

SMILES string

OC[C@H](O)c1ccccc1

InChI

1S/C8H10O2/c9-6-8(10)7-4-2-1-3-5-7/h1-5,8-10H,6H2/t8-/m0/s1

InChI key

PWMWNFMRSKOCEY-QMMMGPOBSA-N

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Application

Intermediate for the synthesis of chiral phosphine catalysts for asymmetric hydrogenations.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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The Journal of Organic Chemistry, 44, 1729-1729 (1979)
J. Chem. Soc. Perkin Trans. II, 489-489 (1982)
Qingsen Hu et al.
Bioresource technology, 101(22), 8502-8508 (2010-07-16)
Saccharomyces cerevisiae JUC15 was successfully obtained by target reaction-oriented screening, which reduced 2-hydroxy-1-phenylethanone (HPE) to (R)-phenyl-1,2-ethanediol ((R)-PED) of excellent enantiomeric excess (e.e. >99.9%). There was no significant decrease in the yield and optical purity of (R)-PED when the free cells
Y Nie et al.
Letters in applied microbiology, 44(5), 555-562 (2007-04-25)
To purify and characterize the (R)-specific carbonyl reductase from Candida parapsilosis; to compare the enzyme with other stereospecific oxidoreductases; and to develop an available procedure producing optically active (R)-1-phenyl-1,2-ethanediol (PED). An (R)-specific carbonyl reductase was found and purified from C.
G P Carlson
Journal of toxicology and environmental health. Part A, 61(8), 709-717 (2001-01-02)
Styrene is a widely used chemical that has been shown to cause lung tumors in mice but not in rats. Styrene toxicity appears to be related to its bioactivation to styrene oxide, and this occurs almost exclusively in Clara cells.

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