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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

Quality Level

200

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

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

FSL

Group 4: Flammable liquids
Type 3 petroleums
Hazardous rank III
Water soluble liquid

JAN Code

122696-3KG:
122696-BULK:
122696-5G:
122696-100G:
122696-500G:
122696-VAR:

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Certificates of Analysis (COA)

Lot/Batch Number
SDBB1155
STBL1455
STBK9988
STBK4828
STBK2790

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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.
Useful methods for the synthesis of isopropylidenes and their chemoselective cleavage.
Vanlaldinpuia K and Bez G.
Tetrahedron Letters, 52(29), 3759-3764 (2011)
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
Renjie Liu et al.
Bioconjugate chemistry, 28(7), 1955-1964 (2017-06-22)
Electrospun biodegradable membranes have attracted great attention for a range of tissue engineering applications. Among them, poly(ε-caprolactone) (PCL) is one of the most widely used polymers, owing to its well-controlled biocompatibility and biodegradability. However, PCL also has a number of
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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