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Sigma-Aldrich

Methyl (R)-3-hydroxybutyrate

99%

Synonym(s):

(-)-(3R)-3-Hydroxybutanoic acid methyl ester, (R)-β-Hydroxybutyric acid methyl ester, Methyl (-)-3-hydroxybutanoate, Methyl (-)-3-hydroxybutyrate, Methyl (3R)-hydroxybutanoate

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About This Item

Linear Formula:
CH3CH(OH)CH2CO2CH3
CAS Number:
3976-69-0
Molecular Weight:
118.13
Beilstein:
6130687
EC Number:
223-610-0
MDL number:
MFCD00063289
UNSPSC Code:
12352108
PubChem Substance ID:
24854601
NACRES:
NA.22

Assay

99%

optical activity

[α]20/D −19.5°, neat

optical purity

ee: 98% (GLC)

refractive index

n20/D 1.421 (lit.)

bp

56-58 °C/11 mmHg (lit.)

density

1.055 g/mL at 20 °C (lit.)

storage temp.

2-8°C

SMILES string

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

InChI

1S/C5H10O3/c1-4(6)3-5(7)8-2/h4,6H,3H2,1-2H3/t4-/m1/s1

InChI key

LDLDJEAVRNAEBW-SCSAIBSYSA-N

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Application

Methyl (R)-3-hydroxybutyrate may be used in the preparation of (R)-(-)-3-hydroxybutanoic acid and poly-(R)-(-)-3-hydroxybutyrate.
Optically active starting material

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

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

Target Organs

Respiratory system

Storage Class Code

10 - Combustible liquids

WGK

WGK 3

Flash Point(F)

163.4 °F - closed cup

Flash Point(C)

73 °C - closed cup

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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Poly[(R)-3-hydroxybutyric acid] natural origin

Sigma-Aldrich

363502

Poly[(R)-3-hydroxybutyric acid]

Synthesis of biodegradable polyesters by polycondensation of methyl (R)-3-hydroxybutyrate and methyl (R)-3-hydroxy-valerate.
Kobayashi T, et al.
Makromol. Chem., Rapid Commun., 14(12), 785-790 (1993)
Direct Degradation of the Biopolymer Poly [(R)-3-Hydroxybutyric Acid] to (R)-3-Hydroxybutanoic Acid and its Methyl Ester.
Seebach D, et al.
Organic Syntheses, 39-39 (1992)
Diya Alsafadi et al.
New biotechnology, 34, 47-53 (2016-05-26)
Olive mill wastewater (OMW), a highly polluting waste from the olive oil industry, was utilized as sole carbon source for the production of polyhydroxyalkanoate (PHA) by extremely halophilic Haloferax Mediterranei (H. mediterranei) in a one stage cultivation step. H. mediterranei
Xiao-Hong Chen et al.
PloS one, 9(4), e94543-e94543 (2014-04-18)
A novel carbonyl reductase (AcCR) catalyzing the asymmetric reduction of ketones to enantiopure alcohols with anti-Prelog stereoselectivity was found in Acetobacter sp. CCTCC M209061 and enriched 27.5-fold with an overall yield of 0.4% by purification. The enzyme showed a homotetrameric

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