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122696

Sigma-Aldrich

DL-1,2-Isopropylideneglycerol

≥97.0%

Synonym(s):

(±)-2,2-Dimethyl-1,3-dioxolane-4-methanol, (±)-2,2-Dimethyl-4-hydroxymethyl-1,3-dioxolane, 1,2-Isopropylidene-rac-glycerol, Solketal

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About This Item

Empirical Formula (Hill Notation):
C6H12O3
CAS Number:
100-79-8
Molecular Weight:
132.16
Beilstein:
104465
EC Number:
202-888-7
MDL number:
MFCD00063238
UNSPSC Code:
12352100
PubChem Substance ID:
24847503
NACRES:
NA.22

Assay

≥97.0%

form

liquid

refractive index

n20/D 1.434 (lit.)

bp

188-189 °C (lit.)

solubility

H2O: miscible
alcohol: miscible
diethyl ether: miscible
oil: miscible
petroleum ether: miscible

density

1.063 g/mL at 25 °C (lit.)

functional group

ether
hydroxyl
ketal

SMILES string

CC1(C)OCC(CO)O1

InChI

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

InChI key

RNVYQYLELCKWAN-UHFFFAOYSA-N

Related Categories

General description

DL-1,2-Isopropylideneglycerol undergoes effective isopropylidenation and deprotection reaction catalyzed by phosphotungstic acid.

Application

DL-1,2-Isopropylideneglycerol was used as the starting reagent for synthesis of tulipaline derivatives.

Legal Information

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Warning

Hazard Statements

H319,H361d

Hazard Classifications

Eye Irrit. 2 - Repr. 2

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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Certificates of Analysis (COA)

Lot/Batch Number
SDBB1155
STBL1455
STBK9988
STBK4828
STBK2790

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Useful methods for the synthesis of isopropylidenes and their chemoselective cleavage.
Vanlaldinpuia K and Bez G.
Tetrahedron Letters, 52(29), 3759-3764 (2011)
Alvise Perosa et al.
Molecules (Basel, Switzerland), 21(2), 170-170 (2016-02-04)
The caprylic, lauric, palmitic and stearic esters of solketal and glycerol formal were synthesized with high selectivity and in good yields by a solvent-free acid catalyzed procedure. No acetal hydrolysis was observed, notwithstanding the acidic reaction conditions.
Thomas Mendgen et al.
Bioorganic & medicinal chemistry letters, 20(19), 5757-5762 (2010-08-24)
The enzyme MurA performs an essential step in peptidoglycan biosynthesis and is therefore a target for the discovery of novel antibacterial compounds. We report here the inhibition of MurA by natural products from tulips (tulipalines and tuliposides), and the structure-activity
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
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)
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