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459941

Sigma-Aldrich

(R)-(−)-Benzoin

98%

Synonym(s):

(R)-2-Hydroxy-2-phenylacetophenone

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About This Item

Linear Formula:
C6H5CH(OH)COC6H5
CAS Number:
5928-66-5
Molecular Weight:
212.24
MDL number:
MFCD00082818
UNSPSC Code:
12352115
PubChem Substance ID:
24869622
Pricing and availability is not currently available.

Assay

98%

optical activity

[α]24/D −115°, c = 1.5 in acetone

optical purity

ee: 99% (HPLC)

mp

135-137 °C (lit.)

functional group

hydroxyl
ketone
phenyl

SMILES string

O[C@H](c1ccccc1)C(=O)c2ccccc2

InChI

1S/C14H12O2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10,13,15H/t13-/m1/s1

InChI key

ISAOCJYIOMOJEB-CYBMUJFWSA-N

Application

(R)-(-)-Benzoin may be used in the preparation of (R)-2-hydroxy-1-phenylpropanone by reacting with benzaldehyde lyase (BAL) in the presence of acetaldehyde.[1]

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
MKCL0777
MKCL0776
MKCD8903
MKCD5901
MKCD4913

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Rüdiger Ohs et al.
Biotechnology progress, 35(6), e2868-e2868 (2019-06-18)
The kinetic description of enzyme-catalyzed reactions is a core task in biotechnology and biochemical engineering. In particular, mechanistic kinetic models help from the discovery of the biocatalyst throughout its application. Chemo- or enantioselective enzyme reactions often undergo two alternative pathways
Hung-Wei Tsui et al.
Journal of chromatography. A, 1637, 461796-461796 (2021-01-03)
The effect of solvents on the enantioselectivities of four structurally similar chiral solutes with a cellulose derivative-based chiral stationary phase, Chiralpak IB, were studied using acetone (AC), 2-propanol (IPA), and tert-butanol (TBA) separately as polar modifiers. The enantioselectivities α of
Rüdiger Ohs et al.
Biotechnology progress, 34(5), 1081-1092 (2018-06-10)
Thiamine diphosphate (ThDP)-dependent enzymes catalyze a broad range of reactions with excellent enantioselectivity. Among these reactions, carboligations of aldehydes are of particular interest since the products, chiral hydroxy ketones, are valuable building blocks in the pharmaceutical industry. However, the substrates

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