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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
Pricing and availability is not currently available.

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[1].

Application

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

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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2-Phenyl-1,3-dioxan-5-ol mixture of cis and trans, ≥97.0% (HPLC)

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13468

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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
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
[Change in behavior of mice and rats under the effect of dimethyl-2,2 hydroxymethyl-4 dioxolanne-1,3 (glycerol acetonide)].
S L Cheav et al.
Annales pharmaceutiques francaises, 44(6), 487-494 (1986-01-01)
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Questions

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  1. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

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  2. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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