キサントフィル

Lutein A

HCID 5281243

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

Lutein127-40-2all-trans-LuteinLutein AVegetable luteinVegetable luteolXantofyltrans-Luteinall-trans-XanthophyllFloraGLOFloraGLO LuteinE 161b
名称をさらに表示
ルテインA植物ルテオールベジタブルルテオール(3R,3'R,6'R)-3,3'-ジヒドロキシ-β,ε-カロテンβ,β-カロテン-3,3'-ジオール3,3'-ジヒドロキシ-β,β-カロテンキサントフィルall-trans-キサントフィルルテイン(3R,3'R,6'R)-ルテインボ-キサン植物ルテインall-trans-(+)-キサントフィル(3R,3'R,6'R)-β,ε-カロテン-3,3'-ジオールall-trans-ルテインtrans-ルテインベジタブルルテインγ-ルテインキサントフィル (〜80%)ルテイン 溶液DimerMARIGOLD EXTRACTLutein 5%DaucolluteochromeXANTHOPHYLL FROM CORNxanthophyllfromalfalfabeta,
Oro Glo 7beta,epsilon-Carotene-3,3'-diol, (3R,3'R,6'R)-LeuteinDTXSID8046749(3R,3'R,6'R)-beta,epsilon-carotene-3,3'-diolOS 24INS NO.161B(I)X72A60C9MT

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

実験および物理化学的性質

LogP7.9
SolubilityInsoluble
Melting Point · 2 件

196

196 °C

Physical Description · 2 件

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

安全と法規制

GHS分類

GHS Classification · 3 件

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 · 3 件

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.

Hazard Classes and CategoriesNot Classified

法規制情報

Regulatory Information · 3 件

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

化学と産業

薬理情報

Pharmacodynamics · 1 件

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 · 1 件

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.

Tissue LocationsAdipose Tissue;Adrenal Gland;Epidermis;Eye Lens;Fibroblasts;Intestine;Neuron;Ovary;Placenta;Retina;Spleen;Testis
Cellular LocationsExtracellular;Membrane

用途と製造

Use Classification · 4 件

Food additives

Food Additives -> COLOUR; NUTRIENT_SUPPLEMENT -> JECFA Functional Classes

Food Additives -> COLOUR -> JECFA Functional Classes

Food Additives -> COLOUR; NUTRIENT_SUPPLEMENT -> JECFA Functional Classes

General Manufacturing Information.beta.,.epsilon.-Carotene-3,3'-diol, (3R,3'R,6'R)-: ACTIVE
応用分野 · 5 件

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.

サプライヤー100 社

国药集团化学试剂有限公司86-21-63210123 · [email protected]
北京华美互利生物化工010-56205725 · [email protected]
成都普瑞法科技开发有限公司+86-028-82633397 18982077548 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]

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

1 件

化合物ノート

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