基本情報
- CAS
127-40-2- 標準SMILES
CC1=C[C@H](O)CC(C)(C)[C@H]1/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)C[C@@H](O)CC1(C)C- InChIKey
KBPHJBAIARWVSC-RGZFRNHPSA-N- 分子式
- C40H56O2
- 平均分子量
- 568.9 g/mol
- 単同位体質量
- 568.42803102
名称と識別子
- 優先名称
- Lutein A
- IUPAC
- (1R)-4-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-18-[(1R,4R)-4-hydroxy-2,6,6-trimethylcyclohex-2-en-1-yl]-3,7,12,16-tetramethyloctadeca-1,3,5,7,9,11,13,15,17-nonaenyl]-3,5,5-trimethylcyclohex-3-en-1-ol
- 現地名
- キサントフィル
- 英語名
- Xanthophyll
- 分子式
- C40H56O2
- 分子量
- 568.87
名称と別名
名称をさらに表示
データベース識別子
- CAS
127-40-2- PubChem CID
- 5281243
- DTXSID
DTXSID8046749- ChEMBL
CHEMBL173929- ChEBI
CHEBI:28838- UNII
- X72A60C9MT
- EC Number
- 204-840-0
- Nikkaji
- J5.394E
物性
構造計算による物性
- XLogP
- 11
- 極性表面積
- 40.5 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 2
- 回転可能結合数
- 10
- 重原子数
- 42
- 形式電荷
- 0
- 複雑度
- 1,270
実験および物理化学的性質
Melting Point
196
196 °C
Physical Description
Dark, yellowish brown liquid
Solid
物理化学的性質
- 融点
- 195 °C · 195 °C
- 比旋光度
- 18 Cd · 18Cd +165° (c = 0.7 in benzene)
- 沸点
- 572.66 °C · 572.66°C (rough estimate)
- 比重(密度)
- 0.9944 · 0.9944 (rough estimate)
- 屈折率
- 20 · n20/D1.361-1.363
- 闪点
- 269.1 · 269.1±27.5 °C
- 貯蔵温度
- -20 °C · -20°C
- 溶解性
- クロロホルム(微量)、ジクロロメタン(微量)、メタノール(微量、加熱、S
- 酸解離定数(Pka)
- 14.61 · 14.61±0.70(Predicted)
- 外見
- 個体
- 色
- 赤から非常に濃い赤
- 由来生物
- rabbit
- Merck
- 13 · 13,10120
- BRN
- 2068547 · 2068547
- 安定性
- 光に敏感、温度に敏感
- 化粧品成分の機能
- スキンコンディショニング
- InChIKey
- KBPHJBAIARWVSC-RGZFRNHPSA-N
- SMILES
- CC(=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C1=C(C)C[C@@H](O)CC1(C)C)\C=C\C=C(C)\C=C\[C@H]2C(C)=C[C@H](O)CC2(C)C
- LogP
- 11.524 · 11.524 (est)
- CAS データベース
- 127 · 127-40-2(CAS DataBase Reference)
- EPAの化学物質情報
- -3 · .beta.,.epsilon.-Carotene-3,3'-diol, (3R,3'R,6'R)- (127-40-2)
安全と法規制
GHS分類
GHS Classification
This chemical does not meet GHS hazard criteria for 95.6% (151 of 158) of all reports.
Not Classified;Reported as not meeting GHS hazard criteria by 151 of 158 companies (only 4.4% companies provided GHS information). For more detailed information, please visit ECHA C&L website.
Aggregated GHS information provided per 158 reports by companies from 4 notifications to the ECHA C&L Inventory.;Reported as not meeting GHS hazard criteria per 151 of 158 reports by companies.;There are 2 notifications provided by 7 of 158 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.
危険有害性情報
Regulatory Information
Chemical: .beta.,.epsilon.-Carotene-3,3'-diol, (3R,3'R,6'R)-
Regulation (EC) No 1333/2008 (amended)
.beta.,.epsilon.-Carotene-3,3'-diol, (3R,3'R,6'R)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
法規制情報
Regulatory Information
Chemical: .beta.,.epsilon.-Carotene-3,3'-diol, (3R,3'R,6'R)-
Regulation (EC) No 1333/2008 (amended)
.beta.,.epsilon.-Carotene-3,3'-diol, (3R,3'R,6'R)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
安全データ
- F
- 1-8-10-16
- wgk
- 3
- tsca
- TSCA listed
- hs_code
- 29061990
- risk_code
- 36/37/38-11
- hazard_code
- Xi
- safety_code
- 26-37/39-16-7-24/25
- ストレージクラス
- 11 - Combustible Solids
化学と産業
薬理情報
Pharmacodynamics
Lutein was found to be present in a concentrated area of the macula, a small area of the retina responsible for central vision. The hypothesis for the natural concentration is that lutein helps protect from oxidative stress and high-energy light. Several studies show that an increase in macula pigmentation decreases the risk for eye diseases such as Age-related Macular Degeneration (AMD).
Mechanism of Action
Xanthophylls have antioxidant activity and react with active oxygen species, producing biologically active degradation products. They also can inhibit peroxidation of membrane phospholipids and reduce lipofuscin formation, both of which contribute to their antioxidant properties. Lutein is naturally present in the macula of the human retina. It filters out potentially phototoxic blue light and near-ultraviolet radiation from the macula. The protective effect is due in part, to the reactive oxygen species quenching ability of these carotenoids. Lutein is more stable to decomposition by pro-oxidants than are other carotenoids such as beta-carotene and lycopene. Lutein is abundant in the region surrounding the fovea, and lutein is the predominant pigment at the outermost periphery of the macula. Zeaxanthin, which is fully conjugated (lutein is not), may offer somewhat better protection than lutein against phototoxic damage caused by blue and near-ultraviolet light radiation. Lutein is one of only two carotenoids that have been identified in the human lens, may be protective against age-related increases in lens density and cataract formation. Again, the possible protection afforded by lutein may be accounted for, in part, by its reactive oxygen species scavenging abilities. Carotenoids also provide protection from cancer. One of the mechanisms of this is by increasing the expression of the protein connexin-43, thereby stimulating gap junctional communication and preventing unrestrained cell proliferation.
用途と製造
Use Classification
Food additives
Food Additives -> COLOUR; NUTRIENT_SUPPLEMENT -> JECFA Functional Classes
Food Additives -> COLOUR -> JECFA Functional Classes
Food Additives -> COLOUR; NUTRIENT_SUPPLEMENT -> JECFA Functional Classes
応用分野
解説キサントフィルは,カロチノイドの一種で、末端のイオノン(ヨノン)環にヒドロキシ基やエポキシド基の形で酸素を含む一群の色素の総称。生体内ではカロチン類の酸化によってつくられる。光合成の際に、補助色素として光のエネルギーの受け渡しをする。緑葉に含まれるキサントフィル類としてはルテインが代表的なものである。黄化して光合成能の低下した葉では酸化のすすんだキサントフィル類が多くなる。アルコールに可溶。緑葉,花,魚卵,卵巣の黄体,カナリアの羽毛など動植物界に広く存在する。動・植物体に広く分布し、植物では花、果実、種子などに色をつける因となる。狭義には最も普通にみられるルテインをさす。クリプトキサンチンやゼアキサンチンも花弁や果実などに広くみいだされる。果皮などにはケトン基をもつ赤色のキサントフィルも低含量ながら広く含まれている。ホオズキ果実のフィザリエンやヤマブキ花弁の黄色色素ヘレニエンは、それぞれゼアキサンチンおよびルテインの脂肪酸エステルである。
解説カロチノイドのうち水酸基,カルボニル基またはエポキシドなどの形で酸素を含むものを総称する。生物界に広く見いだされ,カロチン類の酸素化によって生成されると考えられる。ホオズキ,トウガラシの実の色,卵黄,魚卵,哺乳類の卵巣の黄体などの色はこの色素による。狭義にはルテインluteinで分子式はC40H56O2であり,水酸基をもつゼアキサンチンzeaxanthin,クリプトキサンチンcryptoxanthin,ケト基を有するロドキサンチンrhodoxanthinなどが知られている。株式会社平凡社 世界大百科事典 第2版について 情報
説明Lutein is a dietary carotenoid that has been found in eggs and yellow-colored fruits and vegetables and has diverse biological activities. It reduces hyperglycemia-induced mitochondrial DNA damage and production of reactive oxygen species (ROS) and promotes mitochondrial biogenesis in ARPE-19 cells when used at a concentration of 10 μM. Lutein (20 mg/kg) increases nitric oxide (NO) production and decreases serum levels of endothelin-1 in a rat model of hyperhomocysteinemia. Dietary administration of lutein (0.2%) decreases monocyte migration and lesion size in an ApoE-/- and Ldlr-/- mouse models of atherosclerosis. Lutein reduces infarct size and cardiac malondialdehyde (MDA), lactate dehydrogenase (LDH), and troponin T levels, and increases cardiac levels of catalase (CAT), superoxide dismutase (SOD), heme oxygenase-1 (HO-1), and Nrf2 in a rat model of heart failure induced by isoproterenol . It forms a retinal pigment in human eyes, and high dietary intake of lutein is positively correlated with reduced risk of age-related macular degeneration and cataracts in humans.
使用Xanthophyll is one of the most widespread carotenoid alcohols in nature. Originally isolated from egg yolk, also isolated by chromatography from nettles, algae, and petals of many yellow flowers.
一般的な説明Lutein is a yellow dihydroxylated carotenoid which is found to be a common constituent in many dietary supplements.
上流・下流製品情報
上流原料
サプライヤー100 社
補足説明
定義本品は、卵黄、イラクサ、藻類及び黄色の花弁より得られるカロチノイドアルコールである。
関連反応
化合物ノート
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