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361461

Sigma-Aldrich

meso-2,3-Butanediol

99%

Synonym(s):

(2R,3S)-2,3-Butanediol, (R,S)-2,3-Butanediol, (erythro-) 2,3-Butanediol, rel-(2R,3S)-2,3-Butanediol

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About This Item

Linear Formula:
CH3CH(OH)CH(OH)CH3
CAS Number:
5341-95-7
Molecular Weight:
90.12
Beilstein/REAXYS Number:
1718900
MDL number:
MFCD00077669
UNSPSC Code:
12352100
PubChem Substance ID:
24862226
NACRES:
NA.22

assay

99%

form

solid

bp

183-184 °C (lit.)

mp

32-34 °C (lit.)

storage temp.

2-8°C

SMILES string

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

InChI

1S/C4H10O2/c1-3(5)4(2)6/h3-6H,1-2H3/t3-,4+

InChI key

OWBTYPJTUOEWEK-ZXZARUISSA-N

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General description

meso-2,3-Butanediol is a diol. 2,3-Butanediol (2,3-DB) exists in three stereoisomeric forms: dextro, levo and meso. 2,3-DB is a crucial chemical feedstock and has wide applications in industry. Production of meso-2,3-butanediol under low oxygen condition by metabolically engineered Escherichia coli is reported. 2,3-Butanediol can be converted to 1,3-butadiene, which is used in the preparation of synthetic rubber. meso-2,3-Butanediol is the source of production of 2-butanol by isolates of lactic acid bacteria.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

No data available

flash_point_c

No data available

ppe

Eyeshields, Gloves, type N95 (US)

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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Payam Ghiaci et al.
FEMS microbiology letters, 360(1), 70-75 (2014-09-02)
2-Butanol has been an issue of industries in many areas, for example, biofuel production (as an advanced alternate fuel), fermented beverages, and food (as taste-altering component). Thus, its source of production, the biological pathway, and the enzymes involved are of
Zheng-Jun Li et al.
Applied microbiology and biotechnology, 87(6), 2001-2009 (2010-05-26)
A metabolically engineered Escherichia coli has been constructed for the production of meso-2,3-butanediol (2,3-BD) under low oxygen condition. Genes responsible for 2,3-BD formation from pyruvate were assembled together to generate a high-copy plasmid pEnBD, in which each gene was transcribed
Yuanzhi He et al.
Molecules (Basel, Switzerland), 23(3) (2018-03-23)
(3S)-Acetoin and (2S,3S)-2,3-butanediol are important platform chemicals widely applied in the asymmetric synthesis of valuable chiral chemicals. However, their production by fermentative methods is difficult to perform. This study aimed to develop a whole-cell biocatalysis strategy for the production of
Jong Myoung Park et al.
Microbial cell factories, 12, 20-20 (2013-02-26)
Klebsiella oxytoca, a Gram-negative, rod-shaped, and facultative anaerobic bacterium, is one of the most promising 2,3-butanediol (2,3-BD) producers. In order to improve the metabolic performance of K. oxytoca as an efficient biofactory, it is necessary to assess its metabolic characteristics
Jinshan Li et al.
Applied microbiology and biotechnology, 97(2), 585-597 (2012-08-07)
Paenibacillus polymyxa can produce the (R,R)-stereoisomer of 2,3-butanediol (2,3-BDL) which is industrially very useful. Two important factors affecting (R,R)-BDL production by P. polymyxa ATCC 12321, medium composition, and addition of acetic acid to the culture were investigated in this study
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