9-cis-β,β-カロテン-4-オン

Echinenone

HCID 5281236
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基本情報

CAS
432-68-8
標準SMILES
CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(=O)CCC2(C)C)C(C)(C)CCC1
InChIKey
QXNWZXMBUKUYMD-QQGJMDNJSA-N
分子式
C40H54O
平均分子量
550.9 g/mol
単同位体質量
550.41746635

概要

Echinenone is a carotenone that is beta-carotene in which the 4 position has undergone formal oxidation to afford the corresponding ketone. Isolated as orange-red crystals, it is widely distributed in marine invertebrates. It has a role as a cofactor, an animal metabolite, a marine metabolite and a bacterial metabolite. It derives from a hydride of a beta-carotene.

名称と識別子

優先名称
Echinenone
IUPAC
2,4,4-trimethyl-3-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohexen-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaenyl]cyclohex-2-en-1-one
現地名
9-cis-β,β-カロテン-4-オン
英語名
Echinenone
分子式
C40H54O
分子量
550.86

名称と別名

Echinenone432-68-8all-trans-Echinenoneaphaninmyoxanthin4-oxo-beta-carotene4-keto-beta-caroteneLJ5IO02MNQ2,4,4-trimethyl-3-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohexen-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaenyl]cyclohex-2-en-1-oneCHEBI:4746DTXSID101026555beta-Echinenone
名称をさらに表示
β,β-カロテン-4-オン9'-cis-β,β-カロテン-4-オン9-cis-β,β-カロテン-4-オンβ-エキネノンエキネノンall-trans-エキネノン2,4,4-トリメチル-3-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-テトラメチル-18-(2,6,6-トリメチルシクロヘキサ-1-エン-1-イル)オクタデカ-1,3,5,7,9,11,13,15,17-ノナエン-1-イル]シクロヘキサ-2-エン-1-オン4-ケト-β-カロテン9′-cis-β,β-カロテン-4-オンEinecs 207-083-4β,β-Caroten-4-one?,?-caroten-4-oneEchinenone (In Solution)9-cis-β,β-Carotene-4-one9'-cis-β,β-Carotene-4-one
2,4,4-trimethyl-3-((1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohexen-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaenyl)cyclohex-2-en-1-oneRefChem:920807DTXCID90911095207-083-4beta,beta-Caroten-4-oneEchinenone (Technical Grade).beta.,.beta.-Caroten-4-oneUNII-LJ5IO02MNQ

データベース識別子

CAS
432-68-8
PubChem CID
5281236
DTXSID
DTXSID101026555
ChEBI
CHEBI:4746
UNII
LJ5IO02MNQ
EC Number
207-083-4
Nikkaji
J11.386G

物性

構造計算による物性

XLogP
12.5
極性表面積
17.1 Ų
水素結合供与体数
0
水素結合受容体数
1
回転可能結合数
10
重原子数
41

実験および物理化学的性質

LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C40 isoprenoids (tetraterpenes) [PR0107]

物理化学的性質

融点
178 · 178-180°
沸点
685.3 · 685.3±25.0 °C(Predicted)
比重(密度)
0.972 · 0.972±0.06 g/cm3(Predicted)
貯蔵温度
-20 °C · -20°C
溶解性
クロロホルム（微量）、ジエチルエーテル（微量）、メタノール（微量）
外見
個体

安全と法規制

安全データ

wgk
3
ストレージクラス
11 - Combustible Solids

化学と産業

応用分野 · 2 件

使用Echinenone may be used as an external standard for the extraction of carotenoid from plasma samples. It may also been used as an internal standard, added to samples for extraction and quantification.

一般的な説明Echinenone is a carotenoid with a conjugated carbonyl group. Echinenone (4-keto-β-carotene) is a monoketo compound, is an intermediate between β-carotene and canthaxanthin in animals. It is one of the major carotenoids of Anabaena sp., and also present in Micrococcus roseus. It is located in the thylakoid membrane of Anabaena. The conversion of β-carotene to echinenone is catalysed by CrtO, a β-carotene ketolase.

調製方法 · 1 件

純化方法Purify β,β-caroten-4-one by chromatography on partially deactivated alumina or magnesia, or by using a thin layer plate of silica gel G with 4:1 cyclohexane/diethyl ether as the developing solvent. Recrystallise it from *C6H6/MeOH. Store it in the dark at -20o. The oxime crystallises from *C6H6 with m 208o. [Beilstein 7 III 2858, 7 IV 1881.]

サプライヤー15 社

南京世洲生物科技有限公司025-85560043 15850508050 · [email protected]
上海惠诚生物科技有限公司60498804 18930850192 · [email protected]
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江苏星科元信息科技有限公司400-605-7200 15335295587
上海纽雀客生物科技有限公司13916276291 · [email protected]

補足説明

定義ChEBI: A carotenone that is beta-carotene in which the 4 position has undergone formal oxidation to afford the corresponding ketone. Isolated as orange-red crystals, it is widely distributed in marine invertebrates.

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