3-メチルインドール
3-メチルインドール · 3-メチル-1H-インドール · スカトール · 3メチルインド-ル · SKATOLE 3-メチルインドール スカトール · 3-メチルインドール標準品 · 3‐メチルインドール標準品 · 3-メチルインドール (SKATスカトールN METHANOL (100ΜG/ML)
識別子と物理属性
| CAS No. | 83-34-1 |
|---|---|
| 分子式 | C9H9N |
| 平均分子量 | 131.17 g/mol |
| 単同位体質量 | 131.07349929 g/mol |
| SMILES | Cc1c[nH]c2ccccc12 |
| InChIKey | ZFRKQXVRDFCRJG-UHFFFAOYSA-N |
| PubChem CID | 6736 |
| ChEMBL | CHEMBL1329793 |
| ChEBI | CHEBI:9171 |
| EC No. | 201-471-7 |
| DTXSID | DTXSID8021775 |
| 現地名 | 3-メチルインドール |
化学・物理的性質
| XLogP | 2.6 |
|---|---|
| 極性表面積 | 15.8 |
| 水素結合供与体数 | 1 |
| 水素結合受容体数 | 0 |
| 回転可能結合数 | 0 |
| 重原子数 | 10 |
| 形式電荷 | 0 |
| 複雑度 | 122 |
| 物質分類 | Nitrogen Compounds -> IndolesWaste-water effluent contaminant |
| SpringerMaterials Properties | Angular frequency |
| 香料 | Fragrance Ingredient (Skatole) -> IFRA transparency List |
| LogP（分配係数） | LogP= 2.60 |
| 臭い | CHARACTERISTIC FECAL ODOR AT HIGH LEVELS, BECOMING PLEASANT, SWEET, AND WARM AT VERY LOW LEVELSインドール様の臭い |
| 味 | WARM, OVER-RIPE, FRUITY FLAVOR BELOW 0.1 PPM |
| 食品添加物 | FLAVOR ENHANCER, FLAVORING AGENT OR ADJUVANT -> FDA Substance added to food |
| 香味料 | EU Flavoring substances |
| Color/Form | LEAVES FROM PETROLEUM ETHERWHITE-BROWN SCALESWhite crystalline substance, browning upon aging. |
| 溶解度 | SOL IN HOT WATER, ALC, BENZENE, CHLOROFORM, ETHERSOL IN ACETONE, WATER, ETHANOL, ETHER0.498 mg/mLSoluble in boiling waterSoluble (in ethanol)6.8 [ug/mL] (The mean of the results at pH 7.4)Chloroform (Slightly), Methanol (Slightly)水、エーテル、アルコール、ベンゼン、アセトン、クロロホルムに可溶。 |
| 沸点 | 265-266 °C @ 755 MM HG265.00 to 266.00 °C. @ 755.00 mm Hg265-266 °C (lit.) |
| 融点 | 95 °C97.5 °C92-97 °C (lit.) |
| 密度 | 1.0111 (estimate) |
| 屈折率 | 1.6070 (estimate) |
| FEMA | 3019 | SKATOLE |
| 引火点 | 132 °C |
| 貯蔵条件 | Store below +30°C. |
| 外観・状態 | 結晶性粉末またはフレーク |
| pKa（酸解離定数） | 17.30±0.30(Predicted) |
| 色 | ほぼ白～薄茶色 |
| 臭気閾値 | 0.0000056ppm |
| においのタイプ | 動物 |
| 由来生物 | synthetic |
| Merck | 14,8560 |
| JECFA Number | 1304 |
| BRN | 111296 |
| ヘンリー定数 | 2.9×10-5 mol/(m3Pa) at 25℃, Wetlaufer et al. (1964) |
| 安定性 | 安定していますが、光に敏感です。悪臭！強力な酸化剤、強酸、酸無水物、酸塩化物とは相容れない。可燃性。 |
| 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/C9H9N/c1-7-6-10-9-5-3-2-4-8(7)9/h2-6,10H,1H3 |
| InChIKey | ZFRKQXVRDFCRJG-UHFFFAOYSA-N |
| SMILES | Cc1c[nH]c2ccccc12 |
| LogP（分配係数） | 2.60 |
| CAS データベース | 83-34-1(CAS DataBase Reference) |
| NISTの化学物質情報 | 1H-Indole, 3-methyl-(83-34-1) |
| EPAの化学物質情報 | 3-Methylindole (83-34-1) |
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 76% (304 of 400) of all reports.WarningH315 (19.5%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 400 reports by companies from 16 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| 規制情報 | Chemical: 1H-Indole, 3-methyl-Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)Status: Cease Manufacture Update: 21-11-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/235051H-Indole, 3-methyl-: 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 - 1H-Indole, 3-methyl-: Human health tier I assessment |
| 有害性の概要 | Caused no irritation in humans following 24 hour closed patch test (2% in petrolatum)[HSDB] Lethal doses by intravenous and oral routes produced pulmonary lesions in cattle[RTECS] Safe when used as a flavoring agent in food[JECFA] See Indole. |
| Hazard Classes and Categories | Skin Irrit. 2 (19.5%) |
| 清掃方法 | CHEM SCRUBBING SYSTEMS ARE ATTRACTIVE FOR CONTINUOUSLY HANDLING LARGE VOL OF GAS CONTAINING VERY LOW CONCN OF POTENT ODORANTS. THESE SYSTEMS USUALLY FUNCTION BY OXIDN OF THE ODORANT. THE ODOR CONTROL OF SKATOLE IS DISCUSSED FOR EACH OF THE OXIDIZERS: NAOCL, CL2, KMNO4, AND O3.TWO TYPES OF AIR WASHERS, CROSS-CURRENT AND COUNTERCURRENT, WERE INSTALLED IN THE VENTILATION OF THE EXHAUST SYSTEM IN LIVESTOCK AND POULTRY FARMS, TO DEODORIZE THE AIR. ACTIVATED SLUDGE FROM A SEWAGE PLANT WAS ADDED TO THE CIRCULATING WATER. WASH WATER SAMPLES CONTAINED SKATOLE. |
| 処分方法 | SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices. |
用途
解説
3-methylindole．C9H9N(131.18)．インドールの誘導体．排泄物，ビートの根，ニレ科やクスノキ科のある種の木の幹，コールタール中などに存在する．プロピオンアルデヒドフェニルヒドラゾンC2H5CH=NNHC6H5を塩化亜鉛と加熱して合成する．強い悪臭をもつ白色の葉状晶．融点95 ℃，沸点265～266 ℃．d9941.003．熱水，アルコール類，エーテルに可溶．生体内ではトリプトファンからインドール酢酸を経て生成される．LD50 3450 mg/kg(ラット，経口)．森北出版「化学辞典（第2版）
解説
3-メチルインドールのこと。タール系インドールの高沸点留分や人の排泄物に存在する不快臭をもつ白色葉状晶。融点 95℃。人体ではトリプトファンの分解によって生成する。プロピオンアルデヒドとフェニルヒドラゾンから、塩化亜鉛の存在下で合成される。プロピオンアルデヒドのフェニルヒドラゾンを塩化銅と加熱してつくる。有機溶媒には溶けやすく，松材に対し呈色反応を示す。希薄溶液は芳香をもっているので，花精油の保留剤として用いられる。
用途
インドールと同様に花精油の変調剤、保留剤として少量用いる。
天然物の起源
Skatole is an indole derivative with a strong fecal odor that occurs naturally in feces formed due to the degradation of tryptophan. It is found in several flowers such as jasmine owing to its flowery smell when present in low concentration. Skatole is also one of the key contributors to the development of boar taint in fat samples.Reported found in beetroot, feces, coal tar, Swiss cheese, Gruyere cheese, mozarella cheese, butter, milk, goat and sheep milk, boiled egg, fatty fish, coffee, tea, trassi, rice bran, dried bonito and squid.
使用
3-Methylindole is a naturally abundant pneumotoxin, found primarily in mammalian feces providing its strong fecal odor. In lower concentrations however, the compound has a pleasent aroma, giving orange blossoms and ja smine their pleasing scent. It is often a component of commercial fragrances and perfumes.It helps fluorescent guanosine analogue, which in a dimethoxytrityl, phosphoramidite protected form, can be site-specifically inserted into oligonucleotides through a 3'-5' phosphodiester linkage using an automated DNA synthesizer.
一般的な説明
3-Methylindole (3-MI), commonly found in wine, dairy products, and other foodstuffs, leads to an unpleasant fecal like odor in pig meat products. It is reported to be produced in the intestines of several species by the microbial degradation of tryptophan.
使用用途
低濃度のスカトールは、化粧品調合香料に利用可能です。スカトールは人が嫌う強烈な悪臭ですが、濃度が低いと花のような香りを感じます。 香水の3大フラワー匂いの1つであるジャスミンにもスカトールは含まれており、その香りの中にもかすかに糞尿を感じさせる香りを含んでいます。ただし、多くの人は「甘く柔らかな香り」に感じ、糞尿のような悪臭を感じません。 多くの香水の香料や定着剤のほか、タバコの香料や添加物としても、スカトールを使用可能です。
製法・合成法
製造方法
Prepared synthetically from the phenylhydrazone of propionaldehyde or by cyclization of o-toluidides (Bedoukian, 1967).Industrial synthesis of 3-Methylindole: Propionaldehyde phenylhydrazone is obtained by heating propionaldehyde and phenylhydrazine to remove water molecules, and then heating with zinc chloride or sulfuric acid to remove ammonia molecules to obtain 3-Methylindole.3 Step Synthesis of 3-Methylindole (Skatole) via Hydroboration and Cyclization
純化方法
Crystallise skatole from *benzene or pet ether (m 96.5o). It has also been purified by zone melting. The picrate has m 182o (from Et2O or Et2O/MeOH). [Beilstein 20 III/IV 3206, 20/7 V 69.]