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421626

Sigma-Aldrich

(S)-1,2,3,4-Tetrahydro-3-isoquinolinecarboxylic acid

97%

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About This Item

Empirical Formula (Hill Notation):
C10H11NO2
CAS Number:
74163-81-8
Molecular Weight:
177.20
Beilstein:
4842199
MDL number:
MFCD00144533
UNSPSC Code:
12352106
PubChem Substance ID:
24866388
NACRES:
NA.22

Quality Level

100

Assay

97%

form

solid

optical activity

[α]20/D −168°, c = 1.8 in 1.4 M NaOH

reaction suitability

reaction type: solution phase peptide synthesis

mp

>300 °C (lit.)

application(s)

peptide synthesis

SMILES string

OC(=O)[C@@H]1Cc2ccccc2CN1

InChI

1S/C10H11NO2/c12-10(13)9-5-7-3-1-2-4-8(7)6-11-9/h1-4,9,11H,5-6H2,(H,12,13)/t9-/m0/s1

InChI key

BWKMGYQJPOAASG-VIFPVBQESA-N

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Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

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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B C Wilkes et al.
Biopolymers, 34(9), 1213-1219 (1994-09-01)
A molecular mechanics study (grid search and energy minimization) of the highly delta receptor-selective delta opioid antagonist H-Tyr-Tic-Phe-OH (TIP; Tic: tetrahydroisoquinoline-3-carboxylic acid) resulted in four low energy conformers with energies within 2 kcal/mol of that of the lowest energy structure.
M Manning et al.
Journal of peptide science : an official publication of the European Peptide Society, 1(1), 66-79 (1995-01-01)
We have investigated the effects of mono-substitutions with the conformationally restricted amino acid, 1,2,3,4 tetrahydroisoquinoline-3-carboxylic acid (Tic) at position 3 in arginine vasopressin (AVP), at positions 2, 3 and 7 in potent non-selective cyclic AVP V2/V1a antagonists, in potent and
Raman K Bakshi et al.
Bioorganic & medicinal chemistry letters, 15(14), 3430-3433 (2005-06-14)
The discovery of 1-amino-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid analogs as potent human melanocortin-4 selective agonists is described.
Yingjie Zhang et al.
Current protein & peptide science, 11(8), 752-758 (2011-01-18)
Tic, short for 1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid, is a kind of unnatural α-amino acids. Due to its distinct geometrical conformation and biological activity, the structure of Tic, regarded as the surrogate of proline and the rigid analogue of phenylalanine or tyrosine, has
Kazuya Otake et al.
Chemical & pharmaceutical bulletin, 59(7), 876-879 (2011-07-02)
2-Acyl-tetrahydroisoquinoline-3-carboxylic acid derivatives were synthesized and biologically evaluated. (S)-2-(2,4-Hexadienoyl)-7-[2-(5-methyl-2-phenyloxazol-4-yl)ethoxy]-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (14) showed peroxisome proliferator-activated receptor γ (PPARγ) and PPARα agonist activities and protein-tyrosine phosphatase 1B (PTP-1B) inhibitory activities. PPARγ agonist activity of 14 was comparable to that of rosiglitazone, and
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