アントラニル酸メチル
アントラニル酸メチル · 2-アミノ安息香酸メチル · メチルo-アミノベンゾアート · メチルアントラニラート · o-アミノ安息香酸メチル · アンスラニル酸メチル · メチル アントラnilエト · 2-(メトキシカルボニル)アニリン
識別子と物理属性
| CAS No. | 134-20-3 |
|---|---|
| 分子式 | C8H9NO2 |
| 平均分子量 | 151.16 g/mol |
| 単同位体質量 | 151.06332853 g/mol |
| SMILES | COC(=O)c1ccccc1N |
| InChIKey | VAMXMNNIEUEQDV-UHFFFAOYSA-N |
| PubChem CID | 8635 |
| ChEMBL | CHEMBL1493986 |
| ChEBI | CHEBI:73244 |
| EC No. | 205-132-4 |
| DTXSID | DTXSID6025567 |
| 現地名 | アントラニル酸メチル |
化学・物理的性質
| XLogP | 1.9 |
|---|---|
| 極性表面積 | 52.3 |
| 水素結合供与体数 | 1 |
| 水素結合受容体数 | 3 |
| 回転可能結合数 | 2 |
| 重原子数 | 11 |
| 形式電荷 | 0 |
| 複雑度 | 147 |
| 物質分類 | Nitrogen Compounds -> Aminobenzoic Acids |
| 化粧品 | Masking |
| 香料 | Fragrance Ingredient (Methyl anthranilate) -> IFRA transparency List |
| 農薬 | Other TreatmentActive substance -> EU Pesticides database: Pending |
| LogP（分配係数） | log Kow = 1.88 |
| 臭い | Grape-like odorOrange blossom odorブドウ臭 |
| 味 | Slightly bitter, pungent |
| 食品添加物 | FLAVORING AGENT OR ADJUVANT, SOLVENT OR VEHICLE -> FDA Substance added to food |
| 密度 | 1.1682 at 50 °F (NTP, 1992) - Denser than waterwill sink1.168 at 20 °CDensity: 1.1682 g/cu cm at 10 °C1.161-1.1691.168 g/mL at 25 °C (lit.) |
| 香味料 | EU Flavoring substances |
| Color/Form | CrystalsPale-yellow liquid with bluish fluorescenceColorless to pale-yellow liquid or crystals with bluish fluorescenceColorless to pale yellow liquid or solid |
| 溶解度 | Slightly soluble (NTP, 1992)In water, 2,850 mg/L at 25 °CSlightly soluble in waterVery soluble in ethanol, ethyl etherFreely soluble in alcohol or etherSoluble in fixed oils, propylene glycol, volatile oilsslightly soluble in mineral oilinsoluble in glycerolアルコール: 易溶性(lit.)わずかに溶ける |
| 融点 | 24 °C (lit.) |
| 沸点 | 256 °C (lit.) |
| 蒸気圧 | 1 mm Hg ( 20 °C) |
| 屈折率 | n20/D 1.582(lit.) |
| FEMA | 2682 | METHYL ANTHRANILATE |
| 引火点 | 220 °F |
| 貯蔵条件 | Keep in dark place,Inert atmosphere,Room temperature |
| 外観・状態 | 液体 |
| pKa（酸解離定数） | pK1:2.23(+1) (25°C) |
| 色 | クリアイエローブラウン |
| pH | 7.5-8 (H2O, 20℃)Aqueous solution |
| においのタイプ | フルーティーな |
| 由来生物 | synthetic |
| 爆発限界 | 1.4-7.8%(V) |
| Merck | 14,6020 |
| JECFA Number | 1534 |
| BRN | 606965 |
| ヘンリー定数 | 5.2×100 mol/(m3Pa) at 25℃, Duchowicz et al. (2020) |
| 安定性 | 安定。可燃性。強力な酸化剤とは相容れない。 |
| 主な用途 | フレーバーそして香料 |
| 化粧品成分の機能 | 香料 |
| InChI | 1S/C8H9NO2/c1-11-8(10)6-4-2-3-5-7(6)9/h2-5H,9H2,1H3 |
| InChIKey | VAMXMNNIEUEQDV-UHFFFAOYSA-N |
| SMILES | COC(=O)c1ccccc1N |
| LogP（分配係数） | 1.88 at 20℃ |
| 表面張力 | 43.71 mN/m at 25° |
| CAS データベース | 134-20-3(CAS DataBase Reference) |
| NISTの化学物質情報 | Benzoic acid, 2-amino-, methyl ester(134-20-3) |
| EPAの化学物質情報 | Methyl anthranilate (134-20-3) |
化学的特性
Methyl Anthranilate occurs in a large number of blossom essential oils (e.g., neroli, ylang-ylang, and jasmine oils), grapes, and citrus oils. It occurs as white crystals (mp 24–25°C), or a yellowish liquid, that show blue fluorescence and have an orange blossom odor. Methyl anthranilate is prepared by esterification of anthranilic acid with methanol or by reaction of isatoic anhydride with methanol.It is used in a large number of blossom fragrances. However, its use in perfumes for soaps and cosmetics is limited because it causes discoloration. It is used in flavor compositions (e.g., in grape and citrus flavors).
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 0.2% (4 of 2660) of reports.WarningH319 (99.8%): 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 2660 reports by companies from 13 notifications to the ECHA C&L Inventory. |
|---|---|
| 規制情報 | Chemical: Benzoic acid, 2-amino-, methyl esterCommission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)Benzoic acid, 2-amino-, methyl ester is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzoic acid, 2-amino-, methyl ester are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)Status: Active Update: 24-02-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/19558Benzoic acid, 2-amino-, methyl ester: Does not have an individual approval but may be used under an appropriate group standard |
| その他の安全情報 | IMAP assessments - Benzoic acid, 2-amino-, methyl ester: Human health tier I assessment |
| 火災危険 | This chemical is combustible. (NTP, 1992) |
| 火災の可能性 | Combustible liquid. |
| 健康有害性 | SYMPTOMS: This compound is an irritant to the skin. |
| 有害性の概要 | A mutagen, reproductive effector, and moderate skin irritantCauses somnolence and coma in lethal-dose feeding studies of rats[RTECS] Safe to use as a flavoring agent in foodADI = 0-1.5 mg/kg[JECFA] A skin irritant[CAMEO] A skin and eye irritant[eChemPortal: ERMA] Included in list of fragrance substances with negative human data, i.e. patch tests of patients with suspected contact allergy to fragrance ingredients which yielded negative results.[EC: Scientific Committee on Consumer Safety: Fragrance allergens in cosmetic products (2011)] An irritant[MSDSonline] |
| FDA 要件 | Synthetic flavoring substances and adjuvants /for animal drugs, feeds, and related products/ that are generally recognized as safe for their intended use, within the meaning of section 409 of the Act. Methyl anthranilate is included on this list. |
用途
用途
有機合成原料。
説明
Methyl anthranilate, also known as MA, methyl 2-amino benzoate or carbo methoxy aniline, is an ester of anthranilic acid. Its chemical formula is C8H9NO2.
天然物の起源
Methyl anthranilate naturally occurs in the Concord grapes and other Vitis labrusca grapes or hybrids thereof, and in bergamot, black locust, champaca , gardenia, jasmine, lemon, mandarin, neroli, oranges, rue oil, strawberry, tuberose, wisteria, galangal and ylang ylang. It is also a primary component of the essential apple flavor, along with ethyl acetate and ethyl butyrate.It is also secreted by the musk glands of foxes and dogs, and lends a "sickly sweetness" to the smell of rotting flesh.
使用
Methyl anthranilate acts as a bird repellent. It is food-grade and can be used to protect corn, sunflowers, rice, fruit, and golf courses. Dimethyl anthranilate (DMA) has a similar effect. It is also used for the flavor of grape Kool Aid. It is used for flavoring of candy, soft drinks (e.g. grape soda), gums, and drugs. Methyl anthranilate both as a component of various natural essential oils and as a synthesised aroma-chemical is used extensively in modern perfumery . It is also used to produce Schiff's Bases with aldehydes, many of which are also used in perfumery. In a perfumery context the most common Schiff's Base is known as aurantiol - produced by combining methyl anthranilate and hydroxyl citronellal.
一般的な説明
Clear colorless to tan liquid with an odor of grapes. Has light blue fluorescence.
製法・合成法
製造方法
By heating anthranilic acid and methyl alcohol in the presence of sulfuric acid and subsequent distillation.