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M4001

Sigma-Aldrich

5-Methoxy-DL-tryptophan

≥98% (TLC)

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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

product name

5-Methoxy-DL-tryptophan,

Assay

≥98% (TLC)

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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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
M Leino et al.
Medical biology, 63(4), 160-169 (1985-01-01)
Melatonin and other 5-methoxyindoles are compounds usually associated with the pineal gland. Research is expanding from studies of pineal melatonin to studies of extrapineal organs and of other 5-methoxyindoles besides melatonin. Research in recent years has shown that the retina
N Honda et al.
Proteins, 26(4), 459-464 (1996-12-01)
The wild-type trp repressor of E. coli bound 5-methoxytryptophan, a Trp analogue, less tightly than Trp. A mutant repressor (Val58-->Ala) that should bind 5-methoxytryptophan preferentially to Trp was computationally designed by free-energy calculations accompanied by free-energy decomposition. The designed mutant
M G Balemans et al.
Journal of neural transmission, 49(1-2), 107-116 (1980-01-01)
In the pineal of 21-day old male Wistar rats hydroxyindole-O-methyltransferase (HIOMT) activities involved in the synthesis of several 5-methoxyindoles were determined during the night in April, June, October and January. A high HIOMT activity for the synthesis of melatonin/5-methoxytryptophol was
W F Flight et al.
Journal of neural transmission, 58(3-4), 223-230 (1983-01-01)
In the present study, the synthesis of methoxyindoles in the neural part and in the pigment epithelial layer of the retina of the frog eye was investigated on the basis of naturally occurring substrate at regular intervals during a 24
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