カルミン酸
カルミン酸 · コヒニール · カーミン · カルミン · コチニール · 7-α-D-グルコピラノシル-9,10-ジヒドロ-3,5,6,8-テトラヒドロキシ-1-メチル-9,10-ジオキソ-2-アントラセンカルボン酸 · ナチュラルレッド4 · C.I.ナチュラルレッド4
識別子と物理属性
| CAS No. | 1260-17-9 |
|---|---|
| 分子式 | C22H20O13 |
| 平均分子量 | 492.4 g/mol |
| 単同位体質量 | 492.09039069 g/mol |
| SMILES | Cc1c(C(=O)O)c(O)cc2c1C(=O)c1c(O)c([C@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)c(O)c(O)c1C2=O |
| InChIKey | DGQLVPJVXFOQEV-NGOCYOHBSA-N |
| PubChem CID | 14749 |
| ChEMBL | CHEMBL1366408 |
| EC No. | 215-724-4 |
| 現地名 | カルミン酸 |
化学・物理的性質
| XLogP | 0.5 |
|---|---|
| 極性表面積 | 243 |
| 水素結合供与体数 | 9 |
| 水素結合受容体数 | 13 |
| 回転可能結合数 | 3 |
| 重原子数 | 35 |
| 形式電荷 | 0 |
| 複雑度 | 864 |
| Physical Description | Red crystals in methanolbright red powderdeep red color in water[HSDB] |
| 融点 | 136 °C |
| 比旋光度 | 15654 +51.6° (water) |
| 沸点 | 506.2°C (rough estimate) |
| 密度 | 1.4504 (rough estimate) |
| 屈折率 | 1.6000 (estimate) |
| 引火点 | 12℃ |
| 貯蔵条件 | room temp |
| 溶解度 | 30g/リットル1.298g/L(室温) |
| 外観・状態 | 結晶性粉末 |
| pKa（酸解離定数） | 1.62±0.20(Predicted) |
| 色 | 赤から濃い赤 |
| pH | 1.6 (10g/l, H2O, 20℃) |
| 臭い | 無臭 |
| Merck | 14,1843 |
| BRN | 71651 |
| 主な用途 | 診断アッセイの製造血液学組織学 |
| InChIKey | DGQLVPJVXFOQEV-JNVSTXMASA-N |
| SMILES | Cc1c(C(O)=O)c(O)cc2C(=O)c3c(O)c(O)c([C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)c(O)c3C(=O)c12 |
| LogP（分配係数） | 1.532 (est) |
| CAS データベース | 1260-17-9 |
| EPAの化学物質情報 | C.I. Natural Red 4 (1260-17-9) |
化学的特性
Cochineal extract is a concentrated solution obtained after removing alcohol from an aqueous–alcoholic extract of cochineal (Dactylopius coccus Costa, also called Coccus cati L.). This extract is used as a color additive, the primary colorant being carminic acid.
安全性と法規制
| GHS 分類 | This chemical does not meet GHS hazard criteria for 100% (298 of 298) of all reports.Not ClassifiedReported as not meeting GHS hazard criteria by 298 of 298 companies. For more detailed information, please visit ECHA C&L website.Aggregated GHS information provided per 298 reports by companies from 1 notifications to the ECHA C&L Inventory.Reported as not meeting GHS hazard criteria per 298 of 298 reports by companies.There are 0 notifications provided by 0 of 298 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. |
|---|---|
| 規制情報 | Chemical: CarmineStatus: Active Update: 13-04-2022 https://echa.europa.eu/registration-dossier/-/registered-dossier/28382Carmine: Does not have an individual approval but may be used under an appropriate group standard |
| 有害性の概要 | Anthraquinones are toxic by ingestion and may cause vomiting, diarrhea, kidney and liver damage, and comaDeaths have been reported after children ingested Rhamnus berries[HSDB] Occupational asthma confirmed in workers in dye manufacturing plant[Malo] Cochineal is the dried bodies of the female insect coccus cacti. Carminic acid is the active coloring material, and carmine is the aluminum lake of carminic acid. [HSDB] See Carminic acid and Cochineal. |
| Hazard Classes and Categories | Not Classified |
| 有害作用 | Occupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.Asthma - Reversible bronchoconstriction (narrowing of bronchioles) initiated by the inhalation of irritating or allergenic agents. |
| 水環境危害等級（WGK） | 2 |
| TSCA 収載状態 | TSCA listed |
| 税関コード | 32129000 |
| 化審法 | (9)-301 |
| 安全措置（S） | 22-24/25 |
| 貯蔵分類 | 11 - Combustible Solids |
| 有害物質データ | 1260-17-9(Hazardous Substances Data) |
用途
解説
カルミン酸．サボテン類に寄生するカイガラムシCoccus cactiから単離される動物色素カルミンの成分．アントラキノン誘導体のC-グルコシド．ザクロ色の光沢ある赤色の柱状晶(メタノール)．分解点135 ℃．[α]15654＋51.6°(水)．pKa 1.59±0.20．λmax 278，311(sh)，491，540(sh)nm(log ε 4.50，4.18，3.89，3.64．メタノール)．水，エタノール，エーテル，濃硫酸，水酸化アルカリ溶液に易溶，石油エーテル，ベンゼン，クロロホルムに不溶．アルミニウムイオンやカルシウムイオンとの錯体は深紅色のレーキ顔料となる．絵の具，カラー写真，細菌の染色などに用いられる．
用途
生体染色用。
来歴
CI Natural Red 4(CI 75470), is a red dye occurring as a glycoside in the body of the cochineal insect Dactylopius coccus of the order Homoptera, family Coccidae. This insect is native to Central and South America. The Aztecs had extracted the dye from the insect centuries before the coming of the Spaniards. For breeding purposes, the insects were collected in the autumn and carefully protected during the winter months. Cochineal was harvested after three months, and then the bugs were killed by immersion in hot water, by placing in hot ovens, or by exposure to the hot sun. The latter method produced the highest quality dye. At present, Peru and the Canary Islands are the main source of the dye. Until the advent of synthetic dyes, the principal use for carminic acid was for dyeing tin-mordanted wool or silk. Its aluminum lake, carmine, finds use in the coloring of foods.
使用
Carminic acid (C.I. 75470) For staining nuclei in histological sections. Used to prepare staining solutions. CAS 1260-17-9, pH 1.6 (10g/l, HO, 20°C).
一般的な説明
Dark purplish-brown mass or bright red or dark red powder. Darkens at 248°F. Deep red color in water. Yellow to violet in acidic aqueous solutions.
使用用途
カルミン酸の主成分であるコチニール色素は、菓子類や飲料、水産・畜肉加工肉等の食品に、着色剤として幅広く利用されています。コチニール色素は、動物性の色素で、耐熱性・耐光性に非常に優れています。そのため、要加熱食品や店頭に並べる際に光があたる食品にも用いやすいことが特徴です。 香料や絵の具、カラー写真、細菌の染色などにも用いられています。また、アルミニウムイオンやカルシウムイオンと錯体を形成することで、深紅色のレーキ顔料となります。 さらに、化粧品分野においても、赤色の着色を目的として、洗浄製品や洗顔料、スキンケア化粧品、ヘアスタイリング剤などにも使用可能です。
製法・合成法
純化方法
Carminic acid forms red prisms from EtOH. It gives a red colour in Ac2O and yellow to violet in acidic solution. UV: max (H2O) 500nm ( 6,800); (0.02N HCl) 490-500nm ( 5,800) and (0.0001N NaOH) 540nm ( 3,450). IR: max (Nujol) 1708s, 1693s, 1677m, 1648m, 1632m, 1606s, 1566s, 1509 cm-1. Periodate oxidation is complete after 4hours at 0o with the consumption of 6.2 mols. The tetra-O-methyl carminate has m 186-188o (yellow needles from *C6H6/pet ether). [IR: Ali & Haynes J Chem Soc 1033 1959, Bhatia & Venkataraman Indian J Chem 3 (2) 92 1965, Synthesis: Davis & Smith Biochemical Preparations 4 38 1955, Beilstein 18 III/1V 6697.]