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277460

Sigma-Aldrich

3-(Methylthio)propionaldehyde

96%

Synonym(s):

3-(Methylmercapto)propionaldehyde, 3-(Methylthio)propanal, Methional, NSC 15874

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About This Item

Linear Formula:
CH3SCH2CH2CHO
CAS Number:
3268-49-3
Molecular Weight:
104.17
Beilstein:
1739289
EC Number:
221-882-5
MDL number:
MFCD00007022
UNSPSC Code:
12352100
PubChem Substance ID:
24856764
NACRES:
NA.22

vapor density

>1 (vs air)

Quality Level

100

vapor pressure

760 mmHg ( 165 °C)

Assay

96%

form

liquid

refractive index

n20/D 1.483 (lit.)

bp

165-166 °C (lit.)

density

1.043 g/mL at 25 °C (lit.)

functional group

aldehyde
thioether

storage temp.

2-8°C

SMILES string

CSCCC=O

InChI

1S/C4H8OS/c1-6-4-2-3-5/h3H,2,4H2,1H3

InChI key

CLUWOWRTHNNBBU-UHFFFAOYSA-N

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General description

3-(Methylthio)propionaldehyde (methional) is the major product of chemical methionine conversion via Strecker degradation in food.

Application

3-(Methylthio)propionaldehyde has been used as a reactant in:
  • Oxidative coupling and chemoselective oxidation
  • Intermolecular alkyne hydroacylation reactions
  • Oxidation of sulfides to sulfoxides
It can also be used as a biosynthetic precursor of ethylene.

Pictograms

Skull and crossbonesCorrosion
GHS06,GHS05

Signal Word

Danger

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 4 Inhalation - Acute Tox. 4 Oral - Aquatic Chronic 3 - Eye Dam. 1 - Skin Irrit. 2 - Skin Sens. 1

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 1

Flash Point(F)

165.2 °F - closed cup

Flash Point(C)

74 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKBK3110V
MKBN4367V
04124BE
7930LU
18820JS

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Ethylene formation from methional.
W A Pryor et al.
Biochemical and biophysical research communications, 81(2), 498-503 (1978-03-30)
M M W Etschmann et al.
Applied microbiology and biotechnology, 80(4), 579-587 (2008-07-04)
Yeasts can convert amino acids to flavor alcohols following the Ehrlich pathway, a reaction sequence comprising transamination, decarboxylation, and reduction. The alcohols can be further derivatized to the acetate esters by alcohol acetyl transferase. Using L: -methionine as sole nitrogen
F Amárita et al.
FEMS microbiology letters, 204(1), 189-195 (2001-10-30)
Lactic acid bacteria were screened for methional production from 4-methylthio-2-ketobutanoate. Only Lactococcus lactis IFPL730 produced high amounts of methional. It was demonstrated that production of this compound was an exclusively enzymatic reaction. The present work describes for the first time
A Vallet et al.
Journal of applied microbiology, 104(6), 1833-1840 (2008-01-26)
Determination of pathways involved in synthesis of volatile sulphur compounds (VSC) from methionine by Oenococcus oeni isolated from wine. Production of VSC by O. oeni from methionine was investigated during bacterial cultures and in assays performed in the presence of
Kerstin Burseg et al.
Journal of agricultural and food chemistry, 57(19), 9086-9090 (2009-09-19)
A novel technology (Olfactoscan screening) was applied to screen for volatiles including saturated aldehydes that mask the perception of methional, an off-flavor commonly found in orange juice. For the screening experiment, methional odor pulses were generated by an olfactometer and
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