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
이름 더 보기
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
- 형식 전하
- 0
- 복잡도
- 125
실험 및 물리화학적 성질
LogP
0.8
0.83
Solubility
Soluble
47.6 mg/mL at 20 °C
Soluble in fat; Slightly soluble in water
Soluble (in ethanol)
Boiling Point
209
209.00 °C. @ 760.00 mm Hg
Melting Point
38-43
38 °C
Physical Description
Solid; [Merck Index]
Solid
White crystalline solid; Fresh caramelic nutty, mild tobacco aroma
Kovats Retention Index
1100;1116;1098;1100;1127.1
1141.2;1152.2;1137.4;1139.2;1140.1;1145;1136;1137;1149;1136;1136.6
1743;1779;1739;1779;1767.7;1793;1773.5
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)
- 인화점
- 204 °F · 204 °F
- 저장 조건
- 30 °C · Store below +30°C.
- 용해도
- 2 O: · H2O: 0.1 g/mL, 투명
- 물리적 상태
- 결정 또는 결정성 분말
- 산도 계수 (pKa)
- 3.1 · pKa 3.1 (Uncertain)
- 색상
- 흰색에서 갈색을 띤다
- 냄새
- 10 % · 디프로필렌 글리콜 중 10.00%. 따뜻한 허브 담배
- 냄새 유형
- 약초
- 생물학적 소스
- synthetic
- 수용성
- 무시할 만한
- JECFA Number
- 1320 · 1320
- Merck
- 14 · 14,6100
- BRN
- 113951 · 113951
- 화장품 원료 기능
- 달래는토닉
- InChI
- 1S/C7H7NO2/c1-10-7(9)6-3-2-4-8-5-6/h2-5H,1H3
- InChIKey
- YNBADRVTZLEFNH-UHFFFAOYSA-N
- SMILES
- COC(=O)c1cccnc1
- LogP
- 0.68 at · 0.68 at 25℃
- NIST
- Methyl nicotinate(93-60-7)
- EPA
- Methyl nicotinate (93-60-7)
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
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
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
Hazards Summary
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.
규제 정보
Regulatory Information
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
- hazard_code
- Xi
- safety_code
- 26-36-37/39
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- 스토리지 클래스
- 11 - Combustible Solids
화학 및 산업
약리 정보
Pharmacodynamics
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
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.
Absorption, Distribution and Excretion
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
Use Classification
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
응용 분야
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.
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