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M4001

Sigma-Aldrich

5-Methoxy-DL-tryptophan

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About This Item

Empirical Formula (Hill Notation):
C12H14N2O3
CAS Number:
28052-84-8
Molecular Weight:
234.25
Beilstein:
26781
EC Number:
248-800-0
MDL number:
MFCD00005650
UNSPSC Code:
12352209
PubChem Substance ID:
24896893
NACRES:
NA.26

Assay

≥98% (TLC)

Quality Level

200

form

crystalline

color

white to light beige

mp

258-261 °C (dec.) (lit.)

application(s)

peptide synthesis

storage temp.

−20°C

SMILES string

COc1ccc2[nH]cc(CC(N)C(O)=O)c2c1

InChI

1S/C12H14N2O3/c1-17-8-2-3-11-9(5-8)7(6-14-11)4-10(13)12(15)16/h2-3,5-6,10,14H,4,13H2,1H3,(H,15,16)

InChI key

KVNPSKDDJARYKK-UHFFFAOYSA-N

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Biochem/physiol Actions

5-Methoxy-DL-tryptophan is an amino acid derivative.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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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Anika Kremer et al.
Applied microbiology and biotechnology, 79(6), 951-961 (2008-05-16)
Recently, a gene for a 7-dimethylallyltryptophan synthase (7-DMATS) was identified in Aspergillus fumigatus and its enzymatic function was proven biochemically. In this study, the behaviour of 7-DMATS towards aromatic substrates was investigated and compared with that of the 4-dimethylallyltryptophan synthase
J van Benthem et al.
Journal of neural transmission, 67(1-2), 147-162 (1986-01-01)
Testes weight, plasma FSH and LH concentration and pineal methylating capacity were compared in hamsters housed under either long (LD14:10) or short (LD8:16) photoperiods. Hamsters housed for 14 weeks under short photoperiod showed gonadal atrophy, which was complete after 6
D J Morton
Journal of pineal research, 4(1), 7-11 (1987-01-01)
Pineal glands were incubated in the presence of [3H] methoxytryptophan with and without methoxamine, epinephrine, and norepinephrine. The beta-adrenoceptor-stimulated pineal glands were capable of converting methoxytryptophan to methoxytryptamine, melatonin, methoxyindole acetic acid, and methoxytryptophol, albeit in small quantities. Only methoxyindole
J van Benthem et al.
Journal of neural transmission, 61(3-4), 219-237 (1985-01-01)
Until now the day/night and seasonal rhythmicity in the synthesis of 5-methoxyindoles (MI) is thought to be regulated by environmental factors, especially photoperiod and temperature. Endogenous factors are also implicated in the generation of N-acetyltransferase and hydroxyindole-O-methyltransferase activity rhythms. In
G L Brammer
Life sciences, 55(10), 775-787 (1994-01-01)
Markedly increased melatonin levels in plasma have been observed in response to tryptophan administration. This post-tryptophan melatonin increase has been attributed to the duodenum. Because extra-pineal sources of melatonin may be important in interpreting the meaning of altered melatonin production
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