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Merck
CN

59446

2,3-Isopropylidene-sn-glycerol

purum, ≥97.0% (sum of enantiomers, GC)

Synonym(s):

(R)-(−)-2,2-Dimethyl-1,3-dioxolane-4-methanol, L-α,β-Isopropylideneglycerol

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About This Item

Empirical Formula (Hill Notation):
C6H12O3
CAS Number:
14347-78-5
Molecular Weight:
132.16
UNSPSC Code:
12352000
Beilstein/REAXYS Number:
80117
MDL number:
MFCD00003213

Key Documents

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grade

purum

assay

≥97.0% (sum of enantiomers, GC)

optical activity

[α]/D −13.5±1°, neat

refractive index

n20/D 1.434

bp

75-78 °C/12 mmHg

density

1.064 g/mL at 20 °C (lit.)

storage temp.

2-8°C

SMILES string

CC1(C)OC[C@@H](CO)O1

InChI

1S/C6H12O3/c1-6(2)8-4-5(3-7)9-6/h5,7H,3-4H2,1-2H3/t5-/m1/s1

InChI key

RNVYQYLELCKWAN-RXMQYKEDSA-N

Other Notes

Important key intermediate for the synthesis of GABOB, glycerides and many other compounds; See also 59445 D-enantiomer

Storage Class

10 - Combustible liquids

wgk

WGK 3

flash_point_f

174.2 °F - closed cup

flash_point_c

79 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

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M.E. Jung et al.
Journal of the American Chemical Society, 102, 6304-6304 (1980)
Enzymatic synthesis of 2,3-O-isopropylidene-sn-glycerol, a chiral building block for platelet-activating factor.
H Suemune et al.
Chemical & pharmaceutical bulletin, 34(8), 3440-3444 (1986-08-01)
[Change in behavior of mice and rats under the effect of dimethyl-2,2 hydroxymethyl-4 dioxolanne-1,3 (glycerol acetonide)].
S L Cheav et al.
Annales pharmaceutiques francaises, 44(6), 487-494 (1986-01-01)
P Kanda et al.
Journal of lipid research, 21(2), 257-258 (1980-02-01)
A new procedure for the preparation of 2,3-O-isopropylidene-sn-glycerol is described. L-arabinose is converted to its 4,5-monoisopropylidene diethyl mercaptal derivative. This compound is then subjected to periodate oxidation and borohydride reduction. Following neutralization, the aceton-glycerol is extracted from the aqueous solution
Aldo Jongejan et al.
Biochimica et biophysica acta, 1647(1-2), 297-302 (2003-04-11)
Isotopic substitution provides an effective tool to probe the mechanism of enzyme-catalyzed reactions. To our knowledge, kinetic isotope effects on the enantioselectivity of enzymes have not been reported. We investigated the effect of deuterium substitution on the enantiomeric ratio, E
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