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277460

Sigma-Aldrich

3-(Methylthio)propionaldehyde

96%

Sinonimo/i:

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

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About This Item

Formula condensata:
CH3SCH2CH2CHO
Numero CAS:
3268-49-3
Peso molecolare:
104.17
Beilstein:
1739289
Numero CE:
221-882-5
Numero MDL:
MFCD00007022
Codice UNSPSC:
12352100
ID PubChem:
24856764
NACRES:
NA.22

Densità del vapore

>1 (vs air)

Livello qualitativo

100

Tensione di vapore

760 mmHg ( 165 °C)

Saggio

96%

Stato

liquid

Indice di rifrazione

n20/D 1.483 (lit.)

P. ebollizione

165-166 °C (lit.)

Densità

1.043 g/mL at 25 °C (lit.)

Gruppo funzionale

aldehyde
thioether

Temperatura di conservazione

2-8°C

Stringa SMILE

CSCCC=O

InChI

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

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Descrizione generale

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

Applicazioni

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.

Pittogrammi

Skull and crossbonesCorrosion
GHS06,GHS05

Avvertenze

Danger

Classi di pericolo

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

Codice della classe di stoccaggio

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

Classe di pericolosità dell'acqua (WGK)

WGK 1

Punto d’infiammabilità (°F)

165.2 °F - closed cup

Punto d’infiammabilità (°C)

74 °C - closed cup

Dispositivi di protezione individuale

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

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Certificati d'analisi (COA)

Lot/Batch Number
MKBK3110V
MKBN4367V
04124BE
10522JU
09817MR

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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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