Ethyl Nicotinate

HCID 69188

Basic information

CAS
614-18-6
Standard SMILES
CCOC(=O)c1cccnc1
InChIKey
XBLVHTDFJBKJLG-UHFFFAOYSA-N
Molecular formula
C8H9NO2
Average molar mass
151.16 g/mol
Monoisotopic mass
151.06332853

Overview

Ethyl nicotinate is a member of pyridines and an aromatic carboxylic acid.

Names & identifiers

Preferred name
Ethyl Nicotinate
IUPAC
ethyl pyridine-3-carboxylate
English name
Ethyl nicotinate
Molecular formula
C8H9NO2
Molecular weight
151.16

Names & synonyms

Ethyl nicotinate614-18-6ethyl pyridine-3-carboxylateEthylnicotinate3-Pyridinecarboxylic acid, ethyl esterNicotinic acid, ethyl esterNikethanIgnicutIgnocutMucothermNicaethanNikithan
Show more names
ETHYL 3-PYRIDINECARBOXYLATENICOTINIC ACID ETHYL ESTEREthyl nicotinatethyl nicotinoateETHYL 3-PYRIDINECARBOXYLATE FOR SYNTHESIApamid
Ethyl-nicotinateBa 2673DTXSID9046526NIJ3H353YHNSC-8872DTXCID70265263-carboethoxypyridineRefChem:139015

Database identifiers

CAS
614-18-6
PubChem CID
69188
DTXSID
DTXSID9046526
ChEMBL
CHEMBL2251611
ChEBI
CHEBI:192166
UNII
NIJ3H353YH
EC Number
210-370-7
Nikkaji
J27.971D

Properties

Computed structural properties

XLogP
1.3
Topological polar surface area
39.2 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
3
Rotatable bonds
3
Heavy atoms
11

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Pyridines
CosmeticsSkin conditioning
SpringerMaterials PropertiesChemical shift
LogP1.34
Flavoring AgentsEU Flavoring substances
Physical DescriptionClear light yellow liquid; mp = 8-10 deg C; [Sigma-Aldrich MSDS]

Physicochemical properties

Melting point
8 · 8-10 °C (lit.)
Boiling point
223 · 223-224 °C (lit.)
Density
1.107 g/mL · 1.107 g/mL at 25 °C (lit.)
vapor pressure
4.2 · 4.2-5.5Pa at 20-25℃
refractive index
20 · n20/D 1.504(lit.)
FLAVIS Number
14.11 · 14.110 | Ethyl nicotinate

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H319 (90.3%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)

Aggregated GHS information provided per 1447 reports by companies from 12 notifications to the ECHA C&L Inventory.

Hazard information

Regulatory Information · 4 items

Chemical: 3-Pyridinecarboxylic acid, ethyl ester

Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)

Status: Active Update: 08-03-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/23786

Ethyl 3-pyridinecarboxylate: Does not have an individual approval but may be used under an appropriate group standard

Hazards SummarySafe when used as a flavoring agent in food; [EFSA] An irritant that may cause serious eye injury; [Sigma-Aldrich MSDS] See Nicotinic acid.
Hazard Classes and CategoriesEye Irrit. 2 (90.3%)

Safety data

F
8-9-23
PPE
Eyeshields, Gloves, type ABEK (EN14387) respirator filter
wgk
3
tsca
TSCA listed
hs_code
29333999
Toxicity
LD50 orally in Rabbit: > 2005 mg/kg

Chemistry & industry

Uses & manufacturing

UsesA flavoring agent that naturally occurs in apricots, arctic bramble, beer, and papaya; [EFSA]
Use ClassificationCosmetics -> Skin conditioning
General Manufacturing Information3-Pyridinecarboxylic acid, ethyl ester: ACTIVE
Applications · 3 items

DescriptionEthyl nicotinate is a chemical attractant used to prevent and control plant pests. Ethyl nicotinate was found to be a potent attractant forThrips obscuratus in peaches and apricots. It is more attractive than ripe fruit and catches peak at harvest. Long season trapping demonstrated the efficiency of chemical traps compared to unbaited traps. The attractiveness of the chemical was maintained for at least 2 weeks when 50 μl of the chemical was placed in an open 2 ml vial cap. Various pyralids, geometrids (Lepidoptera), and chironomids (Diptera) were also attracted in low numbers to ethyl nicotinate[1].

UsesEthyl nicotinate is used for skin-conditioning cosmetics. It is principally used in medicine as a local vasodilator at a concentration of 1 to 2 % in creams, ointments and pomades. It is utilized for the treatment sprains, wrenches, muscular pains and tendonitis.

UsesEthyl nicotinate is a nicotinic acid derivative used for skin-conditioning cosmetics.

Preparation methods · 1 item

PreparationNicotinic acid, anhydrous ethanol, and a solid acid catalyst for esterification are added to toluene. The mixture is stirred at 50–65°C for 3–6 hours, then heated and refluxed to separate water. Once no water is discharged, the reaction is complete. The mixture is cooled to room temperature, filtered, and the solid acid catalyst for esterification is recovered. Toluene is recovered from the filtrate under reduced pressure. The resulting light yellow transparent liquid is ethyl nicotinate. The molar ratio of nicotinic acid to anhydrous ethanol is 1:1–1:2, the weight ratio of nicotinic acid to toluene is 1:0.3–1:8, and the amount of solid acid catalyst added is 0.01–0.1 times the weight of nicotinic acid. The solid acid catalyst for esterification is HND230 solid catalyst.

Suppliers100 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
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]
上海泰矶林实业有限公司02150630626 17717886015 · [email protected]

Additional notes

DefinitionChEBI: Ethyl nicotinate is a member of pyridines and an aromatic carboxylic acid.

Related reactions

72 records

Compound notes

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