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480819

Sigma-Aldrich

(R)-(+)-Glycidol

97%, optical purity ee: 98% (GLC)

Synonym(s):

(R)-(+)-Oxirane-2-methanol

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About This Item

Empirical Formula (Hill Notation):
C3H6O2
CAS Number:
57044-25-4
Molecular Weight:
74.08
Beilstein:
79782
EC Number:
404-660-4
MDL number:
MFCD00074873
UNSPSC Code:
12352005
PubChem Substance ID:
24871720
NACRES:
NA.22

Assay

97%

optical activity

[α]23/D +15°, neat

optical purity

ee: 98% (GLC)

impurities

<3% dichloromethane

refractive index

n20/D 1.43 (lit.)

bp

56-57 °C/11 mmHg (lit.)

density

1.116 g/mL at 20 °C (lit.)

storage temp.

−20°C

SMILES string

OC[C@@H]1CO1

InChI

1S/C3H6O2/c4-1-3-2-5-3/h3-4H,1-2H2/t3-/m1/s1

InChI key

CTKINSOISVBQLD-GSVOUGTGSA-N

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General description

Enantioselective esterification of (R)-(+)-glycidol with n-butyric acid in organic media using hybrid gel-entrapped lipase on Celite has been reported.

Application

(R)-(+)-Glycidol may be used in the following synthesis:
  • heteroarylpropane-2,3-diols, useful for combinatorial oligomer synthesis
  • enantiomerically pure (2S,3S)- and (2S,3R)-threoninol and -hydroxyphenylalaninol
  • 2-amino-1,4-anhydro-pentitol and 3-amino-1,5-anhydro-4-deoxy-hexitol with the arabino configuration
  • (S)-4-tosyloxymethyl-2-oxazolidinone, required for the synthesis of protected amino alcohol derivatives
  • 1-(S)-[3-hydroxy-2-(phosphonomethoxy)propyl]cytosine [(S)-HPMPC]
  • chiral building block used to construct an epoxyvinyl iodide intermediate in a synthesis of a furanocembrane, a marine natural product

Signal Word

Danger

Hazard Classifications

Acute Tox. 2 Inhalation - Acute Tox. 4 Dermal - Acute Tox. 4 Oral - Carc. 1B - Eye Dam. 1 - Muta. 2 - Repr. 1B - Self-react. C - Skin Corr. 1B - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

5.2 - Organic peroxides and self-reacting hazardous materials

WGK

WGK 3

Flash Point(F)

161.6 °F

Flash Point(C)

72 °C

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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Tetrahedron Letters, 47, 6401-6401 (2006)
A New Route for Protected Amino Alcohols from (R)-Glycidol. Copper (I) Mediated Alkylation of 4-Tosyloxymethyl-2-oxazolidinone.
Iwama S and Katsumura S.
Bulletin of the Chemical Society of Japan, 67(12), 3363-3365 (1994)
Synthesis of propane-2, 3-diol combinatorial monomers.
Acevedo OL and Andrews RS.
Tetrahedron Letters, 37(23), 3931-3934 (1996)
N Frank et al.
Food additives & contaminants. Part A, Chemistry, analysis, control, exposure & risk assessment, 30(1), 69-79 (2012-10-23)
Glycidyl esters (GEs) are known to be formed during vegetable oil processing. Because of their structure, it has been hypothesised that GEs, like fatty acid esters of chloropropanols (MCPD esters), may be accepted as substrates by gut lipases to release
Hiroshi Honda et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 49(10), 2536-2540 (2011-07-12)
Hemoglobin (Hb) adducts are frequently used to address and/or monitor exposure to reactive chemicals. Glycidol (G), a known animal carcinogen, has been reported to form Hb adducts. Here, we measure G adduct levels in humans who daily ingest DAG oil
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