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277460

Sigma-Aldrich

3-(Methylthio)propionaldehyd

96%

Synonym(e):

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

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About This Item

Lineare Formel:
CH3SCH2CH2CHO
CAS-Nummer:
3268-49-3
Molekulargewicht:
104.17
Beilstein:
1739289
EG-Nummer:
221-882-5
MDL-Nummer:
MFCD00007022
UNSPSC-Code:
12352100
PubChem Substanz-ID:
24856764
NACRES:
NA.22

Dampfdichte

>1 (vs air)

Qualitätsniveau

100

Dampfdruck

760 mmHg ( 165 °C)

Assay

96%

Form

liquid

Brechungsindex

n20/D 1.483 (lit.)

bp

165-166 °C (lit.)

Dichte

1.043 g/mL at 25 °C (lit.)

Lagertemp.

2-8°C

SMILES String

CSCCC=O

InChI

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

InChIKey

CLUWOWRTHNNBBU-UHFFFAOYSA-N

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Allgemeine Beschreibung

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

Anwendung

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.

Piktogramme

Skull and crossbonesCorrosion
GHS06,GHS05

Signalwort

Danger

Gefahreneinstufungen

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

WGK

WGK 1

Flammpunkt (°F)

165.2 °F

Flammpunkt (°C)

74 °C

Persönliche Schutzausrüstung

Faceshields, Gloves, Goggles, type ABEK (EN14387) respirator filter

Analysenzertifikate (COA)

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Sigma-Aldrich

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Sigma-Aldrich

W200700

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Dimethylsulfid ≥99%

Sigma-Aldrich

471577

Dimethylsulfid

Cyclohexancarboxaldehyd 97%

Sigma-Aldrich

108464

Cyclohexancarboxaldehyd

2-Furaldehyd 99%

Sigma-Aldrich

185914

2-Furaldehyd

tert-Butylacrylat contains 10-20 ppm monomethyl ether hydroquinone as inhibitor, 98%

Sigma-Aldrich

327182

tert-Butylacrylat

Tris(2-carboxyethyl)phosphin -hydrochlorid -Lösung 0.5 M, pH 7.0(aqueous solution; pH was adjusted with ammonium hydroxide)

Supelco

646547

Tris(2-carboxyethyl)phosphin -hydrochlorid -Lösung

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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