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:
Molecular Weight:
132.16
UNSPSC Code:
12352005
NACRES:
NA.22
PubChem Substance ID:
EC Number:
244-910-8
Beilstein/REAXYS Number:
80118
MDL number:
Assay:
98%
Form:
liquid
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
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-/m0/s1
InChI key
RNVYQYLELCKWAN-YFKPBYRVSA-N
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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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
European Journal of Organic Chemistry, 1740-1740 (2006)
Global Trade Item Number
| SKU | GTIN |
|---|---|
| 237744-1G | 04061837639364 |
| 237744-5G | 04061838347671 |