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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
Ashutosh Upadhyay et al.
ACS chemical biology, 13(9), 2498-2507 (2018-08-10)
MenJ, annotated as an oxidoreductase, was recently demonstrated to catalyze the reduction (saturation) of a single double bond in the isoprenyl side-chain of mycobacterial menaquinone. This modification was shown to be essential for bacterial survival in J774A.1 macrophage-like cells, suggesting
D McGinty et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 48 Suppl 3, S64-S69 (2010-02-10)
A toxicologic and dermatologic review of 3-methyl-2-buten-1-ol when used as a fragrance ingredient is presented.
Jinhui Yu et al.
Fitoterapia, 83(5), 831-837 (2012-02-07)
Polyprenols with various pharmacological activities were first isolated from Taxus chinensis var. mairei, which is native to China, and were identified by a high performance liquid chromatography/mass spectrometry (HPLC/MS), (1)H nuclear magnetic resonance ((1)H NMR), (13)C NMR and infrared (IR)
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