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Merck
CN

237744

(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:
22323-82-6
Molecular Weight:
132.16
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
24854267
EC Number:
244-910-8
Beilstein/REAXYS Number:
80118
MDL number:
MFCD00063239
Assay:
98%
Form:
liquid

Key Documents

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InChI key

RNVYQYLELCKWAN-YFKPBYRVSA-N

InChI

1S/C6H12O3/c1-6(2)8-4-5(3-7)9-6/h5,7H,3-4H2,1-2H3/t5-/m0/s1

SMILES string

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

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.)

functional group

ether, hydroxyl, ketal

storage temp.

2-8°C

Quality Level

200

Related Categories

General description

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

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. It may also be used to synthesize 1,2-dipalmitoyl-3-benzyl-sn-glycerol and 1-O-(Z)-octadecenyl-sn-glycerol, an intermediate for plasmalogen synthesis.
Used in a synthesis of a chiral allylic triol via extrusion of SO2 from an α,β-epoxysulfone.

Storage Class

10 - Combustible liquids

wgk

WGK 1

flash_point_f

194.0 °F - closed cup

flash_point_c

90 °C - closed cup

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
BCBZ6003
BCBZ5709
BCBW7478
SHBJ2063
SHBJ0793

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European Journal of Organic Chemistry, 1740-1740 (2006)
[58] Synthesis of labeled phospholipids in high yield.
Eibl H, et al.
Methods in Enzymology, 98, 623-632 (1983)
Thermodynamic and kinetic studies of a catalytic process to convert glycerol into solketal as an oxygenated fuel additive.
Nanda MR, et al.
Fuel: The Science and Technology of Fuel and Energy, 117, 470-477 (2014)
Synthesis of Plasmalogen via 2, 3-Bis-O-(4 '-methoxybenzyl)-sn-glycerol.
Qin D, et al.
Journal of the American Chemical Society, 121(4), 662-668 (1999)
Daria Tretiakova et al.
Current drug delivery, 17(4), 312-323 (2020-02-15)
Recently we developed a scalable scheme of synthesis of melphalan ester conjugate with 1,2-dioleoyl-sn-glycerol (MlphDG) and a protocol for the fabrication of its lyophilized liposomal formulation. Herein we compared this new convenient in use formulation of MlphDG with parent drug
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