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237744

Sigma-Aldrich

(S)-(+)-1,2-Isopropylideneglycerol

98%, optical purity ee: 99% (GLC)

Synonym(s):

(S)-(+)-2,2-Dimethyl-1,3-dioxolane-4-methanol, 1,2-Isopropylidene-sn-glycerol, D-α,β-Isopropylideneglycerol, D-(+)-Solketal, D-1,2-O-isopropylidene-sn-glycerol

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About This Item

Empirical Formula (Hill Notation):
C6H12O3
CAS Number:
Molecular Weight:
132.16
Beilstein:
80118
EC Number:
MDL number:
UNSPSC Code:
12352005
PubChem Substance ID:
NACRES:
NA.22

Quality Level

Assay

98%

form

liquid

optical activity

[α]20/D +13.5°, neat

optical purity

ee: 99% (GLC)

refractive index

n20/D 1.434 (lit.)

bp

82-83 °C/14 mmHg (lit.)

density

1.07 g/mL at 25 °C (lit.)

storage temp.

2-8°C

SMILES string

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

General description

(S)-(+)-1,2-Isopropylideneglycerol is a key building block for the synthesis of glycerides and of phosphoglycerides.[1]

Application

(S)-(+)-1,2-Isopropylideneglycerol may be used as a calibration standard during the GC analysis of the solketal yield and glycerol conversion in the ketalization reaction of glycerol and acetone.[2] It may also be used to synthesize 1,2-dipalmitoyl-3-benzyl-sn-glycerol[3] and 1-O-(Z)-octadecenyl-sn-glycerol, an intermediate for plasmalogen synthesis.[4]
Used in a synthesis of a chiral allylic triol via extrusion of SO2 from an α,β-epoxysulfone.[5]

Storage Class Code

10 - Combustible liquids

WGK

WGK 1

Flash Point(F)

194.0 °F - closed cup

Flash Point(C)

90 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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An improved method for the preparation of 1, 2-isopropylidene-sn-glycerol.
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[58] Synthesis of labeled phospholipids in high yield.
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