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122408

Sigma-Aldrich

1,2,3,4-Tetrahydro-1-naphthol

97%

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Synonym(s):
α-Tetralol
Empirical Formula (Hill Notation):
C10H12O
CAS Number:
529-33-9
Molecular Weight:
148.20
Beilstein:
2046227
EC Number:
208-459-0
MDL number:
MFCD00001739
PubChem Substance ID:
24847486
NACRES:
NA.22

Assay

97%

form

solid

refractive index

n20/D 1.564 (lit.)

bp

102-104 °C/2 mmHg (lit.)

density

1.09 g/mL at 25 °C (lit.)

SMILES string

OC1CCCc2ccccc12

InChI

1S/C10H12O/c11-10-7-3-5-8-4-1-2-6-9(8)10/h1-2,4,6,10-11H,3,5,7H2

InChI key

JAAJQSRLGAYGKZ-UHFFFAOYSA-N

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General description

(R)-(-)-enantiomer of 1,2,3,4-Tetrahydro-1-naphthol is a substrate for aryl sulfotransferase (AST) IV enzyme and (S)-(+)-1,2,3,4-tetrahydro-1-naphthol is a competitive inhibitor of AST IV-catalyzed sulfation of 1-naphthalenemethanol. It is the major urinary metabolite of tetralin.

Application

1,2,3,4-Tetrahydro-1-naphthol was used as chiral probe to examine the role of three aromatic residues in enzyme-substrate interactions at the sulfuryl acceptor binding site of aryl sulfotransferase IV enzyme.

Regulatory Information

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Jonathan J Sheng et al.
Drug metabolism and disposition: the biological fate of chemicals, 32(5), 559-565 (2004-04-22)
Aryl sulfotransferase (AST) IV (also named tyrosine-ester sulfotransferase and ST1A1) is a major phenol sulfotransferase in the rat, and it catalyzes the sulfation of many drugs, carcinogens, and other xenobiotics that contain phenol, benzylic alcohol, N-hydroxy arylamine, and oxime functional
Metabolism of tetralin and toxicity of Cuprex in man.
D E Drayer et al.
Drug metabolism and disposition: the biological fate of chemicals, 1(3), 577-579 (1973-05-01)
W F Leebaw et al.
The Journal of clinical endocrinology and metabolism, 47(3), 480-487 (1978-09-01)
Although the role of the neurotransmitter, dopamine (DA), in the regulation of PRL has been well documented, controversy exists regarding its participation in the regulation of the other pituitary hormones. Consequently, we infused DA into six healthy male subjects (ages
Vyas Sharma et al.
Journal of medicinal chemistry, 45(25), 5514-5522 (2002-12-03)
Comparative Molecular Field Analysis (CoMFA) methods were used to produce a 3D-QSAR model that correlated the catalytic efficiency of rat hepatic aryl sulfotransferase (AST) IV, expressed as log(k(cat)/K(m)), with the molecular structures of its substrates. A total of 35 substrate

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