N-バニリルノナンアミド
Nonivamide
基本情報
- CAS
2444-46-4- 標準SMILES
CCCCCCCCC(=O)NCc1ccc(O)c(OC)c1- InChIKey
RGOVYLWUIBMPGK-UHFFFAOYSA-N- 分子式
- C17H27NO3
- 平均分子量
- 293.4 g/mol
- 単同位体質量
- 293.19909372
概要
Nonivamide is a capsaicinoid that is the carboxamide resulting from the formal condensation of the amino group of 4-hydroxy-3-methoxybenzylamine with the carboxy group of nonanoic acid. It is the active ingredient in many pepper sprays. It has a role as a lachrymator. It is a member of phenols and a capsaicinoid.
名称と識別子
- 優先名称
- Nonivamide
- IUPAC
- N-[(4-hydroxy-3-methoxyphenyl)methyl]nonanamide
- 現地名
- N-バニリルノナンアミド
- 英語名
- Nonivamide
- 分子式
- C17H27NO3
- 分子量
- 293.4
名称と別名
NONIVAMIDEN-Vanillylnonanamide2444-46-4PseudocapsaicinPelargonic acid vanillylamideN-VanillylnonamideN-VanillylpelargonamideN-(4-Hydroxy-3-methoxybenzyl)nonanamideNonanoic acid vanillylamideN-Nonanoyl vanillylamideVanillyl pelargonic amideVanillyl-N-nonylamide
名称をさらに表示
N-バニリルノナンアミドN-(3-メトキシ-4-ヒドロキシベンジル)ノナンアミドN-[(4-ヒドロキシ-3-メトキシフェニル)メチル]ノナンアミドノナン酸バニリルアミドノニバミドN-バニリルペラルゴンアミドN-[3-メトキシ-4-ヒドロキシベンジル]ノナンアミドバニリルノナンアミドプソイドカプサイシンペラルゴン酸バニリルアミドバニリルペラルゴン酸アミドN-(4-ヒドロキシ-3-メトキシベンジル)ノナンアミドバニリルn-ノニルアミドノニル酸バニリルアミドヒドロキシメトキシベンジルノナミドN-ペラルゴニルバニリルアミドN-ペラルゴン酸バニリルアミドカプサイシン (合成)ヒドロキシメトキシベンジルペラルゴナミドN‐バニリルノナンアミドSYNTHETIC CAPSAICINCapsaicinoidPAVAcapscaisinNON-4-ENEnonivamide powder
Nonylic acid vanillylamidePelargonyl vanillylamideHydroxymethoxybenzyl pelargonamideN-[(4-hydroxy-3-methoxyphenyl)methyl]nonanamideNonivamidaNonanamide, N-[(4-hydroxy-3-methoxyphenyl)methyl]-Nonanoyl vanillylamideFEMA No. 2787
データベース識別子
- CAS
2444-46-4- PubChem CID
- 2998
- DTXSID
DTXSID1034769- ChEMBL
CHEMBL75124- ChEBI
CHEBI:46936- UNII
- S846B891OR
- EC Number
- 219-484-1
- Nikkaji
- J7.575B
物性
構造計算による物性
- XLogP
- 4.2
- 極性表面積
- 58.6 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 3
- 回転可能結合数
- 10
- 重原子数
- 21
- 形式電荷
- 0
- 複雑度
- 283
実験および物理化学的性質
Chemical ClassesOther Uses -> Food Additives
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals
LipidsFatty Acyls [FA] -> Fatty amides [FA08] -> N-acyl amines [FA0802]
CosmeticsMasking
Fragrances
Fragrance Ingredient (Nonanoyl 4-hydroxy-3-methoxybenzylamide) -> IFRA transparency List
Fragrance
LogP2.96
Food AdditivesFLAVOR ENHANCER, FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Flavoring AgentsEU Flavoring substances
Solubility
Soluble in water (slightly)
slightly
Slightly soluble in water
Soluble (in ethanol)
Human DrugsPharmaceuticals
Melting Point124.00 to 128.00 °C. @ 760.00 mm Hg
Physical Description
Powder with a stinging odor; [Sigma-Aldrich MSDS]
Solid
White powder or crystals; odourless
物理化学的性質
- 融点
- 54 °C · 54°C
- 沸点
- 200 · 200-210 °C(Press: 0.05 Torr)
- 比重(密度)
- 1 · 1,1 g/cm3
- FEMA
- 2787 · 2787 | NONANOYL 4-HYDROXY-3-METHOXYBENZYLAMIDE
- 闪点
- 190 °C · 190°C
- 貯蔵温度
- 2 · Sealed in dry,2-8°C
- 溶解性
- 100 mg/mL、透明からわずかにかすんだ · メタノール: 100 mg/mL、透明からわずかにかすんだ
- 外見
- 粉
- 酸解離定数(Pka)
- 9.76 · 9.76±0.20(Predicted)
- 色
- ホワイトからオフホワイト
- 臭い (Odor)
- 当たり障りのない無臭
- においのタイプ
- 当たり障りのない
- JECFA Number
- 1599 · 1599
- BRN
- 2144300 · 2144300
- 安定性
- 安定。強力な酸化剤とは相容れない。
- 主な用途
- 洗浄剤化粧品フレーバーそして香料食品および飲料パーソナルケア
- 化粧品成分の機能
- 香料
- InChI
- 1S/C17H27NO3/c1-3-4-5-6-7-8-9-17(20)18-13-14-10-11-15(19)16(12-14)21-2/h10-12,19H,3-9,13H2,1-2H3,(H,18,20)
- InChIKey
- RGOVYLWUIBMPGK-UHFFFAOYSA-N
- SMILES
- CCCCCCCCC(=O)NCc1ccc(O)c(OC)c1
- LogP
- 3.43 · 3.43
- CAS データベース
- 2444 · 2444-46-4(CAS DataBase Reference)
- EPAの化学物質情報
- Nonanamide, N-[(4-hydroxy-3-methoxyphenyl)methyl]- (2444-46-4)
化学的性質
化学的特性カプサイシン化学式C18H27NO3はトウガラシに含まれる辛味成分であり特有の刺激感を与える化学物質ですこの物質は人間の味覚受容体に作用し食品の風味を高めるだけでなく多岐にわたる健康効果があると考えられています
化学的特性solid
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
GHS Classification
This chemical does not meet GHS hazard criteria for 0.3% (5 of 1513) of reports.
Danger
H301 (85.7%): Toxic if swallowed [Danger Acute toxicity, oral]
P233, P260, P261, P264, P264+P265, P270, P271, P272, P280, P284, P301+P316, P302+P352, P304+P340, P305+P351+P338, P305+P354+P338, P317, P319, P321, P330, P332+P317, P333+P317, P337+P317, P342+P316, P362+P364, P403, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 1513 reports by companies from 17 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
Regulatory Information
Chemical: Nonanamide, N-[(4-hydroxy-3-methoxyphenyl)methyl]-
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
Nonivamide: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - Nonanamide, N-[(4-hydroxy-3-methoxyphenyl)methyl]-: Human health tier I assessment
Hazards Summary
Effects sensory neurons; [ChemIDplus] Causes lung inflammation in acute inhalation studies of mice; [RTECS] Safe when used as a flavoring agent in food; [JECFA] A skin and strong eye irritant; May cause skin sensitization; [Sigma-Aldrich MSDS] Search for (2444-46-4[EC/RN Number]) AND (sensitizer OR sensitization OR dermatitis OR allergic): no results; [PubMed]
Hazard Classes and CategoriesAcute Tox. 3 (85.7%)
安全データ
- F
- 19
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- RA5998000
- ridadr
- UN 3462 6.1/PG 2
- 毒性
- mouse,LD50,intraperitoneal,8mg/kg (8mg/kg),Journal of Medicinal Chemistry. Vol. 36, Pg. 2595, 1993.
- hs_code
- 29242990
- risk_code
- 25-36/37/38-43
- 化審法
- (9)-993
- hazard_code
- T,Xi
- safety_code
- 26-45-37/39-36/37
- hazard_class
- 6.1
- packing_group
- II
- Hazard Classifications
- Eye Dam. 1Resp. Sens. 1Skin Irrit. 2Skin Sens. 1STOT SE 3
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
PharmacodynamicsRelieves minor aches and pains of muscles and joints,.
Mechanism of Action
Nonivamide is a naturally occurring analog of [DB06774], isolated from peppers, described to produce effects similar to [DB06774]. It is an agonist of the VR1 (vanilloid/TRPV1 receptor). It serves as a transient agonist of these receptors, which are potentiated by pro-inflammatory drugs, a phenomenon that leads to thermal hyperalgesia, or increased heat sensation. Nonivamide has been shown to stimulate afferent neurons with about half the potency of [DB06774]. Agonism of the VR1 (TRPV1) (vanilloid) receptor by Nonivamide was demonstrated to induce the release of Ca2+ from the endoplasmic reticulum (ER) of human lung cells, producing ER stress and cell death [MSDS]. Nonivamide, like other capsaicinoids, acts on the vanilloid receptors located in the peripheral afferent nerve fibers, providing short-acting irritant and algesic properties. Applied dermally, these substances act by stimulating sensitive chemoreceptors of the skin and by reflex, hyperemia and a local elevation in temperature. After repetitive administration, capsaicinoids have been reported to lead to desensitization to nociceptive stimuli possibly by long-acting depletion of peptide neurotransmitters (substance P) from peripheral sensory neurons. Capsaicinoids can modulate muscle tone (in bladder, bronchus etc.). Intravenous injection of nonivamide to rats (10 μg/kg) has been found to lead to bradycardia. The cardiovascular effects are partly explained by substance P release. Nonivamide given to rats subcutaneously (1 mg/kg) was found to cause body temperature decrease, vasodilatation, and increased salivation. Capsaicinoids have shown to illicit bronchospastic effects in guinea pigs. Capsaicin and its analogs were reported to increase barbiturate sleeping time in rats by interacting with hepatic metabolizing enzymes.
Biological Half-LifeAbout 7 minutes.
Metabolism/Metabolites
Limited information is available on pharmacokinetics and metabolism of nonivamide. For the closely related [DB06774] and other capsaicinoids, gastrointestinal absorption is rapid and almost entirely complete in studies of rats (oral dose of about 10 to 15 mg/kg of combined capsaicin and dihydrocapsaicin) with about 85% of the dose being absorbed within 3 hours. Both substances undergo first-pass metabolism in the liver and partly metabolized at the site of absorption.
MeSH Pharmacological ClassificationDrugs that act on neuronal sensory receptors resulting in an increase, decrease, or modification of afferent nerve activity. (From Smith and Reynard, Textbook of Pharmacology, 1991, p367)
Cellular LocationsExtracellular
用途と製造
Uses
Used as a flavoring agent; [FDA]
Use (kg; approx.) in Germany (2009): >50
Use Classification
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Pharmaceuticals
Cosmetics -> Masking
General Manufacturing InformationNonanamide, N-[(4-hydroxy-3-methoxyphenyl)methyl]-: ACTIVE
応用分野
解説ノナン酸バニリルアミドとは、カプサシノイドの一種です。 研究用試薬等で流通する際は、別名の「ノニバミド」がよく用いられます。常温では粉末状の固体で存在しており、白色～うすい赤みの黄色です。 カプサシノイドは、トウガラシに含まれる天然のもの (カプサイシン、ジヒドロカプサイシン、ノルジヒドロカプサイシン等) 以外に合成によって得られるものもあり、ノナン酸バニリルアミドも合成カプサシノイドに該当します。 ノナン酸バニリルアミドもカプサイシンと同様に、皮膚や粘膜に触れると強い刺激性があります。粉末状のノナン酸バニリルアミドは粉塵が舞う可能性高く、使用する際は吸引や皮膚付着への対策が必要です。
用途カプサイシンを含む食品やサプリメントはその健康効果を享受するために様々な形で利用されていますトウガラシを料理に加えることは最も一般的なカプサイシンの摂取方法の一つですまたカプサイシンは局所鎮痛剤としても使用され筋肉痛や関節痛の緩和に役立つクリームやパッチが市販されています
説明Nonanoyl-4-hydroxy-3-methoxybenzylamide is odorless with a pungent, burning taste. Synthesized from nonanyl chloride and vanillylamine.
使用analgesic (topical), depletes Substance P
使用用途ノナン酸バニリルアミドには、カプサイシンと同様に温感作用があるため、湿布薬やパップ剤の温感作用をもたらす成分として有用です。ノナン酸バニリルアミドを使用した湿布薬やパップ剤、液剤などは、貼り付けた場所やその周囲が温まるような感覚を覚えるのが特徴と言えます。
調製方法
製造方法From nonanyl chloride and vanillylamine.
上流・下流製品情報
上流原料
下流製品
補足説明
定義本品は、次の化学式で表される芳香族アミドである。
定義ChEBI: A capsaicinoid that is the carboxamide resulting from the formal condensation of the amino group of 4-hydroxy-3-methoxybenzylamine with the carboxy group of nonanoic acid. It is the active ingredient in many pepper sprays.
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