CAS 4382-54-1 5-Methoxyindole-2-carboxylic acid (HCID 20401)

Overview

5-methoxyindole-2-carboxylic acid is an indolecarboxylic acid that is indole-2-carboxylic acid carrying an additional methoxy substituent at position 5. It has a role as an EC 1.8.1.4 (dihydrolipoyl dehydrogenase) inhibitor, a hypoglycemic agent and a plant metabolite. It is an aromatic ether and an indolecarboxylic acid.

Names & identifiers

Preferred name: 5-Methoxyindole-2-carboxylic acid
IUPAC: 5-methoxy-1H-indole-2-carboxylic acid
English name: 5-METHOXYINDOLE-2-CARBOXYLIC ACID
Molecular formula: C10H9NO3
Molecular weight: 191.18

Names & synonyms

5-Methoxyindole-2-carboxylic acid4382-54-15-Methoxy-1H-indole-2-carboxylic acidINDOLE-2-CARBOXYLIC ACID, 5-METHOXY-NSC 30927EINECS 224-487-6AFK8L54HA2NSC-30927CHEBI:133222DTXSID401959445-Methoxy-2-indolateRefChem:103063

Show more names

5-MeO-ICAAKOS JY2083529TIMTEC-BB SBB0036355-METHOXYINDOL-2-CARBOXYLIC ACID5-methoxy-indole-2-carboxylicaci5-methoxy-2-indolecarboxylicacid5-Methoxy-2-indolecarboxylic acid

5-Methoxy-2-indolecarboxylate5-Methoxyindole-2-carboxylateDTXCID80101847DTXCID80118435224-487-61H-Indole-2-carboxylic acid, 7-methoxy-24610-33-1DTXSID50179356

Database identifiers

CAS: 4382-54-1
PubChem CID: 20401
DTXSID: DTXSID40195944
ChEMBL: CHEMBL23961
ChEBI: CHEBI:133222
UNII: AFK8L54HA2
EC Number: 224-487-6
Nikkaji: J41.036E

Properties

Computed structural properties

XLogP: 2.3
Topological polar surface area: 62.3 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 3
Rotatable bonds: 2
Heavy atoms: 14
Formal charge: 0
Complexity: 231

Physicochemical properties

Melting point: 199 · 199-201 °C (lit.)
Boiling point: 326.92 °C · 326.92°C (rough estimate)
Density: 1.2722 · 1.2722 (rough estimate)
refractive index: 1.531 · 1.5310 (estimate)
storage temp.: Keep in dark place,Sealed in dry,Room Temperature
pka: 4.38 · 4.38±0.30(Predicted)
form: Powder
color: Light yellow to brownish
BRN: 157478 · 157478
InChI: InChI=1S/C10H9NO3/c1-14-7-2-3-8-6(4-7)5-9(11-8)10(12)13/h2-5,11H,1H3,(H,12,13)
InChIKey: YEBJVSLNUMZXRJ-UHFFFAOYSA-N
SMILES: N1C2=C(C=C(OC)C=C2)C=C1C(O)=O
CAS DataBase Reference: 4382 · 4382-54-1(CAS DataBase Reference)
EWG's Food Scores: 1 · 1
FDA UNII: 8 L54HA2 · AFK8L54HA2
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H315-H319-H335
Precautionary statements: 261 · P261-P305+P351+P338
PPE: 95 · Eyeshields, Gloves, type N95 (US)
Safety Statements: 22 · 22-24/25
WGK Germany: 3 · 3
RTECS: 6005000 · NL6005000
HazardClass: IRRITANT
HS Code: 29339900 · 29339900
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 50% (1 of 2) of reports.

Warning

H315 (50%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesSkin Irrit. 2 (50%)

Safety data

PPE: Eyeshields, Gloves, type N95 (US)
wgk: 3
rtecs: NL6005000
hs_code: 29339900
Signal word: Warning
Symbol(GHS): GHS07
safety_code: 22-24/25
hazard_class: IRRITANT
Storage Class: 11 - Combustible Solids
Hazard statements: H302-H315-H319-H335
Precautionary statements: P261-P305+P351+P338

Chemistry & industry

Applications · 3 items

UsesReactant for preparation of:• ;Anticancer agents1• ;A fluorescent small molecule probe for in vivo lipid imaging2• ;Indoleamine 2,3-dioxygenase (IDO) inhibitors3• ;Selective Dopamine D3 receptor ligands4• ;5-HT4 receptor ligands5• ;Inhibitors of Mycobacterium tuberculosis pantothenate synthetase6• ;Hypoxia selective cytotoxins7• ;Potent antitumor bifunctional DNA alkylating agents8

Uses5-Methoxyindole-2-carboxylic Acid is a very useful synthetic intermediate. It is a reactant used to prepare anticancer agents, Indoleamine 2,3-dioxygenase (IDO) inhibitors, and potent antitumor bifunctional DNA alkylating agents.

UsesReactant for preparation of:Anticancer agentsA fluorescent small molecule probe for in vivo lipid imagingIndoleamine 2,3-dioxygenase (IDO) inhibitorsSelective Dopamine D3 receptor ligands5-HT4 receptor ligandsInhibitors of Mycobacterium tuberculosis pantothenate synthetaseHypoxia selective cytotoxinsPotent antitumor bifunctional DNA alkylating agents

Upstream & downstream products

Upstream raw materials

Carbon dioxide 1H-Indole, 2-bromo-5-methoxy-Tetrahydrofuran ISOPROPYLMAGNESIUM CHLORIDE n-Butyllithium Hexane

Downstream products

5-Methoxyindole

Suppliers100 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

陕西缔都新材料有限公司81124267 17392282731 · [email protected]

上海炎泽化工有限公司15345144255 19975051755 · [email protected]

苏州启航生物科技有限公司18151111370 · [email protected]

Additional notes · 1 item

DefinitionChEBI: 5-methoxyindole-2-carboxylic acid is an indolecarboxylic acid that is indole-2-carboxylic acid carrying an additional methoxy substituent at position 5. It has a role as a plant metabolite, a hypoglycemic agent and an EC 1.8.1.4 (dihydrolipoyl dehydrogenase) inhibitor. It is an indolecarboxylic acid and an aromatic ether.