D-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid
- Product Name
- D-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid
- CAS No.
- 103733-65-9
- Chemical Name
- D-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid
- Synonyms
- D-TIC;H-D-TIC-OH;Atebant Impurity 4;RARECHEM BK PT 0079;Icatibant Impurity 4;D-PHENYLALANINE ANALOGUE;D-1,2,3,4-Tetrahydroisoquinoline;Tetrahydroisoquinoline-3-carboxylic acid;D-1,2,3,4-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID;1,2,3,4-D-TETRAHYDROISOQUINOLINE-3-CARBOXYLIC ACID
- CBNumber
- CB7397017
- Molecular Formula
- C10H11NO2
- Formula Weight
- 177.2
- MOL File
- 103733-65-9.mol
D-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid Property
- Melting point:
- 320-323 °C (decomp)
- Boiling point:
- 372.0±42.0 °C(Predicted)
- Density
- 1.225±0.06 g/cm3(Predicted)
- storage temp.
- Keep in dark place,Inert atmosphere,Room temperature
- solubility
- Aqueous Acid (Slightly), Aqueous Base (Sparingly, Sonicated)
- form
- Crystalline Powder
- pka
- 2.21±0.20(Predicted)
- color
- White
- InChI
- 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-/m1/s1
- InChIKey
- BWKMGYQJPOAASG-SECBINFHSA-N
- SMILES
- C1C2=C(C=CC=C2)C[C@H](C(O)=O)N1
- CAS DataBase Reference
- 103733-65-9(CAS DataBase Reference)
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P302+P352IF ON SKIN: wash with plenty of soap and water.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- T294825
- Product name
- (R)-(+)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid
- Packaging
- 250mg
- Price
- $50
- Updated
- 2021/12/16
- Product number
- C6784
- Product name
- (R)-1,2,3,4-Tetrahydro-3-isoquinolinecarboxylicacid
- Packaging
- 100mg
- Price
- $60
- Updated
- 2021/12/16
- Product number
- OR14710
- Product name
- (R)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid
- Purity
- 98%
- Packaging
- 25g
- Price
- $169
- Updated
- 2021/12/16
- Product number
- 02598
- Product name
- (3)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid
- Purity
- ≥ 99% (assay)
- Packaging
- 25G
- Price
- $80
- Updated
- 2021/12/16
- Product number
- 02598
- Product name
- (3)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid
- Purity
- ≥ 99% (assay)
- Packaging
- 1G
- Price
- $10
- Updated
- 2021/12/16
D-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid Chemical Properties,Usage,Production
Description
D-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid ((3R)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid) is a magnetic, neutral compound. It is used as a pharmacological study to investigate the reaction mechanism and kinetics of the deuteration process. The asymmetric synthesis of D-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid has been investigated using vinylene chloride and hydantoin as reactants. There are various parameters that affect the kinetics of this reaction such as solvent type and temperature. The nitric oxide synthase inhibitor activity of D-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid has been studied in vitro. Results have shown that it inhibits nitric oxide synthase by binding to the heme iron of the enzyme and preventing the conversion of arginine
Chemical Properties
White solid
Uses
(R)-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic Acid, is an amino acid building block used in peptide synthesis. With a growing peptide drug market the fast, reliable synthesis of peptides is of great importance.
Definition
ChEBI: D-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid is a member of isoquinolines.
Synthesis
50-00-0
673-06-3
103733-65-9
General procedure for the synthesis of (R)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid from formaldehyde and D-phenylalanine: 1. Preparation of (3R)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid: D-phenylalanine (50 g, 0.3 mol), concentrated hydrochloric acid (386 mL), and 37% wt formalin (113.7 mL) were mixed, and the reaction was carried out for 4 h at 95 °C with vigorous stirring. Upon completion of the reaction, the mixture was cooled to room temperature and stirring was continued for 2 hours. The reaction mixture was filtered and the precipitate was washed with cold water to afford (3R)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (25 g, 42% yield) in white solid form. 2. Esterification reaction: benzyl alcohol (64 g) and p-toluenesulfonic acid (26.9 g) were added to the above product, and the reaction was carried out under reflux in a Dean-Stark apparatus with benzene (400 mL) as solvent. After completion of the reaction, the solvent was removed in vacuum and the crude product was ground with ether to obtain a solid, which was subsequently recrystallized with water and methanol to give (R)-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid (28 g, 35% yield) in white solid form.
References
[1] MedChemComm, 2014, vol. 5, # 9, p. 1381 - 1383
[2] Journal of Medicinal Chemistry, 1988, vol. 31, # 11, p. 2092 - 2097
[3] Patent: WO2004/72086, 2004, A2. Location in patent: Page 182
[4] Journal of Medicinal Chemistry, 2010, vol. 53, # 15, p. 5727 - 5737
D-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from D-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid manufacturers
- Product
- D-1,2,3,4-Tetrahydroisoquinoline-3-carboxylic acid 103733-65-9
- Price
- US $0.00/kg
- Min. Order
- 1kg
- Purity
- 98%
- Supply Ability
- Customise
- Release date
- 2025-11-19
- Product
- D-Tic-OH 103733-65-9
- Price
- US $0.00-0.00/kg
- Min. Order
- 1kg
- Purity
- 98%;99%
- Supply Ability
- 1T+
- Release date
- 2023-09-08
- Product
- D-TIC 103733-65-9
- Price
- US $1.00/g
- Min. Order
- 1g
- Purity
- 98%
- Supply Ability
- 100KG
- Release date
- 2019-07-23