메틸니코티네이트

Methyl Nicotinate

HCID 7151CAS 93-60-7

기본 정보

표준 SMILES
COC(=O)c1cccnc1
InChIKey
YNBADRVTZLEFNH-UHFFFAOYSA-N
분자식
C7H7NO2
평균 분자량
137.14 g/mol
단동위원소 질량
137.04767847

이름 및 식별자

우선 이름
Methyl Nicotinate
IUPAC
methyl pyridine-3-carboxylate
현지명
메틸니코티네이트
영어명
Methyl nicotinate
분자식
C7H7NO2
분자량
137.14

이름 및 동의어

METHYL NICOTINATE93-60-7methyl pyridine-3-carboxylateMethylnicotinateMethyl-nicotinateMethyl 3-pyridinecarboxylate3-Pyridinecarboxylic acid, methyl ester3-(Methoxycarbonyl)pyridineHeat sprayNicotinic acid, methyl ester3-(Carbomethoxy)pyridineFEMA No. 3709
이름 더 보기
메틸니코티네이트NICOTINIC ACID METHYL ESTERFEMA 3709NicomethNikometMethyl niacinMethyl nicotiteMethyl nictinateAKOS BBS-00004415
3-Pyridinecarboxylic acid methyl esterDTXSID70444717B1AVU9DJNNSC-13126DTXCID5024471VitathoneRefChem:157960202-261-8

데이터베이스 식별자

CAS
93-60-7
PubChem CID
7151
DTXSID
DTXSID7044471
ChEMBL
CHEMBL379845
ChEBI
CHEBI:134761
UNII
7B1AVU9DJN
EC Number
202-261-8
Nikkaji
J39.098D

물성

구조 계산 물성

XLogP
0.8
극성 표면적
39.2 Ų
수소 결합 공여자 수
0
수소 결합 수용자 수
3
회전 가능 결합 수
2
무거운 원자 수
10

실험 및 물리화학적 성질

LogP · 2건

0.8

0.83

Solubility · 4건

Soluble

47.6 mg/mL at 20 °C

Soluble in fat; Slightly soluble in water

Soluble (in ethanol)

Boiling Point · 2건

209

209.00 °C. @ 760.00 mm Hg

Melting Point · 2건

38-43

38 °C

Vapor Pressure0.27 [mmHg]
Physical Description · 3건

Solid; [Merck Index]

Solid

White crystalline solid; Fresh caramelic nutty, mild tobacco aroma

물리화학적 성질

녹는점
42 · 42-44 °C (lit.)
끓는 점
204 °C · 204 °C (lit.)
밀도
1.2528 · 1.2528 (rough estimate)
증기압
0.4 hPa · 0.4 hPa (25 °C)
FEMA
3709 · 3709 | METHYL NICOTINATE
굴절률
1.5323 · 1.5323 (estimate)

화학적 성질

Methyl nicotinate is white to brownish crystals or crystalline powder and has a fresh, caramellic, nutty and mild tobacco odor.

안전 및 규제

GHS 분류

GHS Classification · 6건

This chemical does not meet GHS hazard criteria for 0.8% (13 of 1623) of reports.

Warning

H315 (98.6%): Causes skin irritation [Warning Skin corrosion/irritation];H319 (99.1%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364 (click each P-code to see the statement)

Aggregated GHS information provided per 1623 reports by companies from 13 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Reported as not meeting GHS hazard criteria per 13 of 1623 reports by companies.;There are 12 notifications provided by 1610 of 1623 reports by companies with hazard statement code(s).;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.

유해성 정보

Regulatory Information · 4건

Chemical: 3-Pyridinecarboxylic acid, methyl ester

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

Status: Cease Manufacture Update: 08-02-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/19335;Status: Active Update: 28-09-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/20643

Methyl nicotinate: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to human health
Hazards Summary · 1건

Erythema provoked is basis of a methylnicotinate test of anti-inflammatories. [ChemIDplus] Contact irritant that causes non-immunologic contact reactions; [ToxPlanet: DOD] Safe when used as a flavoring agent in food; [JECFA] A skin and strong eye irritant; [Sigma-Aldrich MSDS] See Ethyl nicotinate and Methyl isonicotinate.

Hazard Classes and CategoriesSkin Irrit. 2 (98.6%);Eye Irrit. 2 (99.1%)

규제 정보

Regulatory Information · 4건

Chemical: 3-Pyridinecarboxylic acid, methyl ester

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

Status: Cease Manufacture Update: 08-02-2019 https://echa.europa.eu/registration-dossier/-/registered-dossier/19335;Status: Active Update: 28-09-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/20643

Methyl nicotinate: Does not have an individual approval but may be used under an appropriate group standard

안전 데이터

wgk
3
tsca
TSCA listed
rtecs
QT1925000
독성
LD50 orally in Rabbit: > 2000 mg/kg
HS 번호
29333999
risk_code
36/37/38-36/38

화학 및 산업

약리 정보

Protein BindingNo pharmacokinetic data available.
Pharmacodynamics · 1건

Following topical administration, methyl nicotinate acts as a peripheral vasodilator to enhance local blood flow at the site of application. It induced vasodilation of the peripheral blood capillaries which are located in the dermal papillae of upper dermis layers adjacent to the epidermis–dermis junction. During tissue penetration at the dermis, methyl nicotinate is hydrolyzed to nicotinic acid. In human volunteers, topical administration of methyl nicotinate caused vasodilation-induced generalized cutaneous erythema.

Mechanism of Action · 1건

While the mechanism of action of methyl nicotinate and other topically-administered nicotinic acid esters is not clear, it is thought that methyl nicotinate promotes the release of prostaglandin D2 that is strictly locally-acting due to its short half-life. It was demonstrated in human subjects that the local cutaneous vascular response to methyl nicotinic was suppressed by inhibitors of prostaglandin biosynthesis, indicating that the effect of methyl nicotinate on vascular smooth muscles may be mediated by the release of local prostaglandins. Prostaglandins released from the skin and blood vessels induce cutaneous vasodilation.

Biological Half-Life_In vitro_, the half-life of methyl nicotinate in the dermis was 3 to 10 minutes.
Metabolism/MetabolitesMethyl nicotinate undergoes ester hydrolysis to form nicotinic acid and methanol. The hydrolysis is thought to be mediated by nonspecific α-naphthylacetate-esterase at the dermis layer of the skin.
Absorption, Distribution and Excretion · 4건

The presence of methyl group facilitates the penetration of methyl nicotinate through the skin with good lipophilicity, allowing rapid absorption following topical administration. _In vitro_, about 80-90% of the polar compounds methyl nicotinate rapidly penetrated the skin. It was demonstrated in excised skin of hairless mice that methyl nicotinate can effectively bypass the stratum corneum layer of the skin. In humans, nicotinic acid and nicotinamide were shown to be rapidly absorbed from the stomach and intestine via a sodium carrier-mediated mechanism at low concentrations.

Following epicutaneous administration of small radiolabelled dose of methyl nicotinate in human volunteers, approximately 15% of the dose was recovered in the urine within 108 hours after treatment. The excretion of nicotinic acid mainly takes place in the kidneys.

According to the animal studies, nicotinic acid is mainly concentrated in the liver, kidneys, and adipose tissue.

No pharmacokinetic data available.

용도 및 제조

UsesUsed as a rubefacient; [Merck Index] Topical vasodilator used to test the efficacy of skin protection compounds (i.e. products designed to provide barriers to chemical warfare agents); [DOD] Used as a flavoring agent; [FDA]
Use Classification · 6건

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Cosmetics -> Soothing; Tonic

General Manufacturing Information3-Pyridinecarboxylic acid, methyl ester: ACTIVE
응용 분야 · 4건

개요Methyl nicotinate is a skin irritant in man, in particular producing vasodilatation, which is used on purpose in “rubefacient”, to produce a redness or inflammation for a short period of time, often in lip plumper or other lip products. Methyl nicotinate is also an active ingredient of a number of veterinary preparations intended for topical application as a rubefacient for the treatment of a variety of diseases, such as respiratory diseases, vascular disorders (oedema, haematoma), and rheumatoid disorders in cattle and horses (doses not stated; the concentration in the formulated veterinary medicinal product is 2%).

출처Reported found in ground coffee, roasted filberts, guanabana (Annona muicata L.), roasted peanuts, wild strawberries, vanilla bean, papaya, guava, plum, beer cognac, soursop, malt, wort, Bourbon vanilla and mountain papaya.

용도Methyl nicotinate (MN) is the methyl ester of nicotinic acid that is used as an active ingredient, a rubefacient and counter-irritant in over-the-counter topical preparations indicated for the temporary relief of aches and pains in muscles,tendons, and joints. The action of methyl nicotinate as a rubefacient is thought to involve peripheral vasodilation.For veterinary purposes,methyl nicotinate is used to treat respiratory diseases, vascular disorders, rheumatoid arthritis, and muscle and joint pains.Methyl nicotinate can be found in in guava fruit, papaya, strawberry, soursop(Annona muricata), beer, grape brandy, coffee, roasted filbert, roasted peanut and Bourbon vanilla.

일반 설명Methyl nicotinate (or nicotinic acid methyl ester) is used as a rubefacient for the relief of pains in muscles, tendons, and joints. It is also used in food as a flavoring agent.

공급사50 곳

北京华美互利生物化工010-56205725 · [email protected]
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]
上海泰矶林实业有限公司02150630626 17717886015 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]

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