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162353

Sigma-Aldrich

3-Methyl-2-buten-1-ol

99%

Synonym(s):

3,3-Dimethylallyl alcohol, Prenol

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About This Item

Linear Formula:
(CH3)2C=CHCH2OH
CAS Number:
556-82-1
Molecular Weight:
86.13
Beilstein:
1633479
EC Number:
209-141-4
MDL number:
MFCD00002916
UNSPSC Code:
12352100
eCl@ss:
39020334
PubChem Substance ID:
24849980
NACRES:
NA.22

vapor pressure

1.4 mmHg ( 20 °C)

Assay

99%

form

liquid

expl. lim.

16.3 %

refractive index

n20/D 1.443 (lit.)

bp

140 °C (lit.)

density

0.848 g/mL at 25 °C (lit.)

SMILES string

C\C(C)=C\CO

InChI

1S/C5H10O/c1-5(2)3-4-6/h3,6H,4H2,1-2H3

InChI key

ASUAYTHWZCLXAN-UHFFFAOYSA-N

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General description

3-Methyl-2-buten-1-ol reacts with nitrosocarbonyl benzene to yield 5-hydroxy-isoxazolidines. It is commonly used as fragrance ingredient.

Application

3-Methyl-2-buten-1-ol was used as starting reagent during asymmetric total syntheses of (R)-(+)- and (S)-(-)-umbelactone via Sharpless asymmetric epoxidation reaction.

Signal Word

Danger

Hazard Classifications

Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Eye Dam. 1 - Flam. Liq. 3 - Skin Corr. 1B - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

3 - Flammable liquids

WGK

WGK 1

Flash Point(F)

124.7 °F - closed cup

Flash Point(C)

51.5 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Anastasia Zerva et al.
Molecules (Basel, Switzerland), 23(9) (2018-09-22)
Feruloyl esterases (FAEs, E.C. 3.1.1.73) are biotechnologically important enzymes with several applications in ferulic acid production from biomass, but also in synthesis of hydroxycinnamic acid derivatives. The use of such biocatalysts in commercial processes can become feasible by their immobilization
Hong Liang et al.
Metabolic engineering, 65, 223-231 (2020-11-29)
Engineering microbes to utilize non-conventional substrates could create short and efficient pathways to convert substrate into product. In this study, we designed and constructed a two-step heterologous ethanol utilization pathway (EUP) in Escherichia coli by using acetaldehyde dehydrogenase (encoded by
Branko Radetich et al.
Journal of the American Chemical Society, 124(11), 2430-2431 (2002-03-14)
A solution is reported to the classic unsolved problem of stereoselective synthesis of all-E oligoprenols, such as E-farnesylfarnesol, by a cationic coupling analogous to the biosynthetic pathway. The simplicity and efficacy of the method, which is outlined in Scheme 1
Vijay Gnanadesikan et al.
Journal of the American Chemical Society, 130(25), 8089-8093 (2008-05-23)
An effective strategy has been developed for the efficient site-selective epoxidation of poylolefinic isoprenoid alcohols, based on the use of an internal control element for intramolecular reaction. The approach is illustrated by application to a series of polyisoprenoid alcohols (polyprenols)
Lan Yang et al.
Fitoterapia, 82(6), 834-840 (2011-05-21)
The hepatoprotective effects of polyprenols from Ginkgo biloba L. leaves were evaluated against carbon tetrachloride induced hepatic damage in Sprague-Dawley rats. The elevated levels of serum ALT, AST, ALP, ALB, TP, HA, LN, TG, and CHO were restored towards normalization
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