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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)

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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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
Ethylene formation from methional.
W A Pryor et al.
Biochemical and biophysical research communications, 81(2), 498-503 (1978-03-30)
M Murata et al.
Japanese journal of cancer research : Gann, 90(3), 268-275 (1999-06-08)
Adduct formation has been considered to be a major causal factor of DNA damage by carcinogenic heterocyclic amines. By means of experiments with 32P-labeled DNA fragments and an electrochemical detector coupled to a high-pressure liquid chromatograph, we investigated whether the
Rong Di et al.
Journal of agricultural and food chemistry, 51(19), 5695-5702 (2003-09-04)
The primary flavor compound in potato, methional, is synthesized from methionine by the Strecker degradation reaction. A major problem associated with potato processing is the loss of methional. Methional or its precursor, methionine, is not added back during potato processing
D Perrin et al.
Archives of biochemistry and biophysics, 377(2), 266-272 (2000-06-14)
Both peroxynitrous acid and peroxynitrite react with methionine, k(acid) = (1.7 +/- 0.1) x 10(3) M(-1) s(-1) and k(anion) = 8.6 +/- 0.2 M(-1) s(-1), respectively, and with N-acetylmethionine k(acid) = (2.8 +/- 0.1) x 10(3) M(-1) s(-1) and k(anion)
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