CAS 3471-31-6 5-Methoxyindoleacetic acid (HCID 18986)

Names & identifiers

Preferred name: 5-Methoxyindoleacetic acid
IUPAC: 2-(5-methoxy-1H-indol-3-yl)acetic acid
English name: 5-Methoxyindole-3-acetic acid
Molecular formula: C11H11NO3
Molecular weight: 205.21

Names & synonyms

5-Methoxyindole-3-acetic acid3471-31-62-(5-methoxy-1H-indol-3-yl)acetic acid5-Methoxyindoleacetic acidMethoxyindoleacetic acidMSN7CK6ETHDTXSID70188268CHEBI:28281RefChem:536732DTXCID00110759222-438-35-Methoxy-3-indoleacetic acid

Show more names

5-MeO-IAA5-methoxyindoleaceticacid2-(5-Methoxy-3-indolyl)acetic acid5-Methoxy-IAATIMTEC-BB SBB003497RARECHEM AL BO 14665-Mehtoxyindoleacetic acid5-Methoxy-3-indolaceticacid5-methoxy-indole-3-aceticaci5-Methoxyindol-3-ylessigsure

5-Methoxyindoleacetate5-Methoxyindol-3-ylacetic acidMFCD000056381H-Indole-3-acetic acid, 5-methoxy-(5-Methoxy-1H-indol-3-yl)acetic acid5-Methoxyindole-3-aceticacidINDOLE-3-ACETIC ACID, 5-METHOXY-UNII-MSN7CK6ETH

Database identifiers

CAS: 3471-31-6
PubChem CID: 18986
DTXSID: DTXSID70188268
ChEMBL: CHEMBL85433
ChEBI: CHEBI:28281
UNII: MSN7CK6ETH
EC Number: 222-438-3
Nikkaji: J139.625K

Properties

Computed structural properties

XLogP: 1.4
Topological polar surface area: 62.3 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 3
Rotatable bonds: 3
Heavy atoms: 15
Formal charge: 0
Complexity: 244

Experimental & physicochemical properties

Physical DescriptionSolid

Collision Cross Section144 Å² [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

Physicochemical properties

Melting point: 145 · 145-148 °C (dec.)(lit.)
Boiling point: 343.88 °C · 343.88°C (rough estimate)
Density: 1.2235 · 1.2235 (rough estimate)
refractive index: 1.513 · 1.5130 (estimate)
storage temp.: -20 °C · Keep in dark place,Sealed in dry,Store in freezer, under -20°C
solubility: DMSO (Slightly), Methanol (Slightly)
pka: 4.52 · 4.52±0.30(Predicted)
form: crystalline
color: light yellow to tan
Water Solubility: insoluble
BRN: 187161 · 187161
InChI: InChI=1S/C11H11NO3/c1-15-8-2-3-10-9(5-8)7(6-12-10)4-11(13)14/h2-3,5-6,12H,4H2,1H3,(H,13,14)
InChIKey: COCNDHOPIHDTHK-UHFFFAOYSA-N
SMILES: N1C2=C(C=C(OC)C=C2)C(CC(O)=O)=C1
CAS DataBase Reference: 3471 · 3471-31-6(CAS DataBase Reference)
FDA UNII: 7 CK6ETH · MSN7CK6ETH
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302+H312+H332
Precautionary statements: 261 · P261-P264-P270-P271-P280-P301+P312+P330-P302+P352+P312+P362+P364-P304+P340+P312-P501
PPE: 95 · Eyeshields, Gloves, type N95 (US)
Safety Statements: 24 · 24/25
WGK Germany: 3 · 3
RTECS: 3660500 · NL3660500
HS Code: 29339900 · 29339900
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

GHS classification

GHS Classification · 5 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]；H312 (50%): Harmful in contact with skin [Warning Acute toxicity, dermal]；H315 (50%): Causes skin irritation [Warning Skin corrosion/irritation]；H319 (50%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]；H332 (100%): Harmful if inhaled [Warning Acute toxicity, inhalation]；H335 (50%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, 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.；Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (100%)；Acute Tox. 4 (50%)；Skin Irrit. 2 (50%)；Eye Irrit. 2A (50%)；Acute Tox. 4 (100%)；STOT SE 3 (50%)

Safety data

PPE: Eyeshields, Gloves, type N95 (US)
wgk: 3
rtecs: NL3660500
hs_code: 29339900
Signal word: Warning
Symbol(GHS): GHS07
safety_code: 24/25
Storage Class: 11 - Combustible Solids
Hazard statements: H302+H312+H332
Precautionary statements: P261-P264-P270-P271-P280-P301+P312+P330-P302+P352+P312+P362+P364-P304+P340+P312-P501

Chemistry & industry

Pharmacology

Cellular LocationsCytoplasm

Metabolite PathwaysTryptophan metabolism

Applications · 3 items

UsesReactant for preparation of aryloxybenzothiazoles as inhibitors of NO production 1 Reactant for preparation of transcription inhibitors of novel Gli1 as antitumor agents Reactant for preparation of indole derivatives as NR2B/NMDA receptor antagonists 2 Reactant for preparation of indolyl esters and amides related to indomethacin as selective COX-2 inhibitors 3 Reactant for preparation of quinoline salicylic acid series of P-selectin antagonists 4 Reactant for preparation of prostaglandin D2 receptor antagonists.

Uses5-Methoxyindole-3-acetic Acid is a chemical reagent used in the analysis of the physiological properties of auxins.

UsesReactant for preparation of aryloxybenzothiazoles as inhibitors of NO productionReactant for preparation of transcription inhibitors of novel Gli1 as antitumor agentsReactant for preparation of indole derivatives as NR2B/NMDA receptor antagonistsReactant for preparation of indolyl esters and amides related to indomethacin as selective COX-2 inhibitorsReactant for preparation of quinoline salicylic acid series of P-selectin antagonistsReactant for preparation of prostaglandin D2 receptor antagonists

Suppliers100 total

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

衢州润东化工有限公司0570-8789886 18892685668 · [email protected]

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

湖南韵邦生物科技股份有限公司85561037 15386497078 · [email protected]

上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]

Additional notes · 1 item

DefinitionChEBI: 5-methoxyindole-3-acetic acid is a member of the class of indole-3-acetic acids in which the hydrogen at position 5 of indole-3-acetic acid has been replaced by a methoxy group. It has a role as a Brassica napus metabolite, a human urinary metabolite, an antibacterial agent, a marine xenobiotic metabolite, a carcinogenic agent and a rat metabolite. It is a member of indole-3-acetic acids and an aromatic ether.