488216
3,4-Dihydroxy-1-butene
≥99%
Synonym(s):
3-Butene-1,2-diol
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About This Item
Linear Formula:
CH2=CHCH(OH)CH2OH
CAS Number:
Molecular Weight:
88.11
Beilstein:
1633578
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
Assay
≥99%
bp
195 °C/733 mmHg (lit.)
density
1.047 g/mL at 25 °C (lit.)
functional group
hydroxyl
SMILES string
OCC(O)C=C
InChI
1S/C4H8O2/c1-2-4(6)3-5/h2,4-6H,1,3H2
InChI key
ITMIAZBRRZANGB-UHFFFAOYSA-N
Related Categories
General description
3,4-Dihydroxy-1-butene, also known as 3-butene-1,2-diol (BDdiol), is a metabolite of 1,3-butadiene. It forms the precursor for synthesizing different chiral building blocks. BDdiol can undergo oxidation to form hydroxymethylvinyl ketone (HMVK). 1,2-epoxy-3-butene (EB) on hydrolysis in the presence of epoxide hydrolases (EH) forms BDdiol.
Application
3,4-Dihydroxy-1-butene can be used:
- As a reactant to synthesize cyclic organic carbonates by continuous flow procedure.
- To prepare substituted oxazolidinone ligands used to target medicinally relevant RNAs.
Signal Word
Warning
Hazard Statements
Precautionary Statements
Hazard Classifications
Acute Tox. 4 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral
Storage Class Code
10 - Combustible liquids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Versatile and scalable synthesis of cyclic organic carbonates under organocatalytic continuous flow conditions
Gerardy R, et al.
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Gregory M Sandala et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 15(19), 4865-4873 (2009-03-28)
High-level conventional ab initio and density functional theory (DFT) calculations have been performed to examine the fate of the native substrate glycerol (1) and its analogue but-3-ene-1,2-diol (7) in the coenzyme B(12)-dependent enzyme glycerol dehydratase (GDH). Experimental studies find that
X Cheng et al.
Drug metabolism and disposition: the biological fate of chemicals, 21(1), 121-124 (1993-01-01)
A rapid, simple extraction and GC assay procedure is described that allows quantitation of micromolar concentrations of butadiene bisoxide and 3-butene-1,2-diol in microsomal suspensions exposed to butadiene. Butane-1,4-diol is used as the internal standard. The recovery of these compounds from
R J Krause et al.
Chemical research in toxicology, 14(12), 1590-1595 (2001-12-18)
The metabolic fate of 3-butene-1,2-diol (BDD), a secondary metabolite of the industrial carcinogen, 1,3-butadiene, is unclear. The current study characterizes BDD oxidation to hydroxymethylvinyl ketone (HMVK), a reactive Michael acceptor. Because of its instability in aqueous medium, HMVK was trapped
E Malvoisin et al.
Xenobiotica; the fate of foreign compounds in biological systems, 12(2), 137-144 (1982-02-01)
1. In rat liver microsomes, 1,3-butadiene was metabolized to butadiene monoxide, which was subsequently transformed into 3-butene-1,2-diol by microsomal epoxide hydrolase. 2. In the metabolism of butadiene oxide in microsomes, four metabolites were detected, namely two stereoisomers of DL-diepoxybutane, and
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