Tryptophol

HCID 10685
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Basic information

CAS
526-55-6
Standard SMILES
OCCc1c[nH]c2ccccc12
InChIKey
MBBOMCVGYCRMEA-UHFFFAOYSA-N
Molecular formula
C10H11NO
Average molar mass
161.2 g/mol
Monoisotopic mass
161.08406397

Overview

Tryptophol is an indolyl alcohol that is ethanol substituted by a 1H-indol-3-yl group at position 2. It has a role as an auxin, a Saccharomyces cerevisiae metabolite and a plant metabolite.

Names & identifiers

Preferred name
Tryptophol
IUPAC
2-(1H-indol-3-yl)ethanol
English name
Tryptophol
Molecular formula
C10H11NO
Molecular weight
161.2

Names & synonyms

Tryptophol526-55-6Indole-3-ethanol3-(2-Hydroxyethyl)indole1H-Indole-3-ethanol2-(1H-Indol-3-yl)ethanol3-IndolylethanolIndoleethanolIndole ethanolDTXSID20601735809LZ7G1UNSC-3884
Show more names
2-(1H-INDOL-3-YL)ETHAN-1-OLIEAB-3-INDOLYLETHANOLBETA-3-INDOLYLETHANOLDK803NSC 3884
CHEBI:17890RefChem:900693DTXCID1041219208-393-23-Indoleethanol2-(3-Indolyl)ethanolEthanol, 2-indol-3-yl-1H-Indolyl-3-ethanol

Database identifiers

CAS
526-55-6
PubChem CID
10685
DTXSID
DTXSID2060173
ChEMBL
CHEMBL226545
ChEBI
CHEBI:17890
UNII
5809LZ7G1U
EC Number
208-393-2
Nikkaji
J6.661C

Properties

Computed structural properties

XLogP
1.8
Topological polar surface area
36 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
1
Rotatable bonds
2
Heavy atoms
12

Experimental & physicochemical properties

Chemical ClassesBiological Agents -> Amino Acids and Derivatives
Melting Point59 °C
Physical Description · 2 items

Solid; [Merck Index] Brown or yellow solid; [Alfa Aesar MSDS]

Solid

Collision Cross Section · 2 items

133.6 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]

133.8 Ų [M+H]+

Physicochemical properties

Melting point
56 · 56-59 °C(lit.)
Boiling point
174 °C · 174 °C (2.02527 mmHg)
Density
1.084 · 1.0840 (rough estimate)
refractive index
1.52 · 1.5200 (estimate)
Flash point
255 °C · 255 °C
storage temp.
Keep in dark place,Sealed in dry,Room Temperature

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 50% (2 of 4) of reports.

Warning

H302 (25%): Harmful if swallowed [Warning Acute toxicity, oral]

P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, 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 4 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazards SummaryCauses somnolence in intraperitoneal lethal-dose studies of mice (LD50 = 351 mg/kg); [RTECS] May cause irritation; [Alfa Aesar MSDS]
Hazard Classes and CategoriesAcute Tox. 4 (25%)

Safety data

F
8
PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
tsca
TSCA listed
rtecs
KL3685000
hs_code
29339990

Chemistry & industry

Uses & manufacturing

General Manufacturing Information1H-Indole-3-ethanol: ACTIVE
Applications · 2 items

UsesTryptophol is a metabolite formed in the liver after disulfiram treatment that induces sleep in humans. It is also a secondary product of alcoholic fermentation.

UsesReactant for preparation of:Inhibitors of the C-terminal domain of RNA polymerase II and their antitumor activitiesAnti-HIV-1 agentsInhibitors of Protein-Protein InteractionsPartial agonists of the serotonin 5-HT1A receptorGrowth hormone secretagoguesVascular endothelial growth factor (VEGF) inhibitorsA2B adenosine receptor ligandsPotential detoxification inhibitors of the crucifer phytoalexin brassininInhibitors of interleukine 6Dual binding site acetylcholinesterase inhibitors

Upstream & downstream products

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]
T&W GROUP021-61551611 13296011611 · [email protected]
武汉科美沃化工有限公司+86-2785736489 +8618171418573 · [email protected]
Hebei Yanxi Chemical Co., Ltd.+86-17531190177 · [email protected]

Additional notes

DefinitionChEBI: An indolyl alcohol that is ethanol substituted by a 1H-indol-3-yl group at position 2.

Related reactions

98 records
New reaction record

Compound notes

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