CAS 116-31-4 Retinal (HCID 638015)

概要

All-trans-retinal is a retinal in which all four exocyclic double bonds have E- (trans-) geometry. It has a role as a gap junctional intercellular communication inhibitor, a mouse metabolite and a human metabolite. It is a vitamin A and a retinal.

名称と識別子

優先名称: Retinal
IUPAC: (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenal
現地名: レチナール
英語名: Retinal
分子式: C20H28O
分子量: 284.44

名称と別名

all-trans-Retinalretinaltrans-Retinal116-31-4retinaldehydevitamin A aldehyderetineneaxerophthalall-E-RetinalE-RetinalRetinene 1all-trans-Retinaldehyde

名称をさらに表示

E-レチナール(2E,4E,6E,8E)-3,7-ジメチル-9-(2,6,6-トリメチル-1-シクロヘキセン-1-イル)-2,4,6,8-ノナテトラエナールレチネン1(2E,4E,6E,8E)-3,7-ジメチル-9-(2,6,6-トリメチル-1-シクロヘキセニル)-2,4,6,8-ノナテトラエナールレチネンall-trans-レチンアルデヒド(2E,4E,6E,8E)-9-(2,6,6-トリメチル-1-シクロヘキセニル)-3,7-ジメチル-2,4,6,8-ノナテトラエナールtrans-レチナールall-trans-レチナールall-transレチナールアキセロフタールビタミンA3レチンアルデヒドtrans-ビタミンAアルデヒドビタミンAアルデヒド全トランスレチナールビタミンA1アルデヒドレチナール ALL-TRANSALL TRANS-レチナールレチナールNanoactive RALRetinylaldehydeRetinene1

Vitamin A1 aldehydeall-trans-Vitamin A aldehydeall-trans-RetineneRetinyl aldehydeRetinal, all-trans(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenal(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenalDTXSID5025998

データベース識別子

CAS: 116-31-4、472-86-6
PubChem CID: 638015
DTXSID: DTXSID5025998
ChEMBL: CHEMBL81379
ChEBI: CHEBI:17898
UNII: RR725D715M
EC Number: 204-135-8
Nikkaji: J1.003.612G、J1.826.581H、J5.279E、J861.440G

物性

構造計算による物性

XLogP: 6.2
極性表面積: 17.1 Å²
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: 5
重原子数: 21
形式電荷: 0
複雑度: 522

実験および物理化学的性質

LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> Retinoids [PR0109]

CosmeticsPersonal care product

SpringerMaterials PropertiesAngular frequency

Melting Point63 °C

Physical DescriptionSolid

Collision Cross Section · 2 件

170.1 Å² [M+H]+ [CCS Type: DT; Method: single field calibrated with Agilent tune mix (Agilent)]

165.39 Å² [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

物理化学的性質

融点: 61 · 61-63°C
沸点: 366.92 °C · 366.92°C (rough estimate)
比重(密度): 1.0083 · 1.0083 (rough estimate)
屈折率: 1.45 · 1.4500 (estimate)
貯蔵温度: -20 °C · -20°C
溶解性: クロロホルム（微量）、酢酸エチル（微量）、メタノール（微量）
外見: 粉
色: 黄色
由来生物: synthetic (organic)
水溶解度: 70 mg/L · <70mg/L(25℃)
安定性: 吸湿性、光感受性、温度感受性
化粧品成分の機能: スキンコンディショニング
InChI: InChI=1S/C20H28O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,15H,7,10,14H2,1-5H3/b9-6+,12-11+,16-8+,17-13+
InChIKey: NCYCYZXNIZJOKI-OVSJKPMPSA-N
SMILES: C(=O)/C=C(/C=C/C=C(/C=C/C1C(C)(C)CCCC=1C)\C)\C
CAS データベース: 116 · 116-31-4(CAS DataBase Reference)
EPAの化学物質情報: Retinal (116-31-4)

化学的性質

化学的特性Yellow Powder

安全と法規制

GHS分類

GHS Classification · 4 件

Danger

H302 (28.6%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P264, P270, P273, P280, P301+P317, P302+P352, P318, P321, P330, P332+P317, P362+P364, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 147 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

危険有害性情報

Hazard Classes and CategoriesAcute Tox. 4 (28.6%)

安全データ

wgk: 3
tsca: TSCA listed
rtecs: VH6407000
hs_code: 29122990
risk_code: 22-38
化審法: 新規公示化学物質（2011年3月31日以前届出）
hazard_code: Xn
safety_code: 22-36/37

化学と産業

薬理情報

Metabolism/MetabolitesRetinal has known human metabolites that include Tretinoin.

Tissue LocationsAdrenal Cortex

Cellular LocationsCytoplasm

Metabolite PathwaysRetinol Metabolism

用途と製造

General Manufacturing InformationRetinal: ACTIVE

応用分野 · 3 件

解説レチナール，黄色の柱状晶．融点61～64 ℃．λmax 369.5 nm(log ε 4.64)．淡水産の魚類，両生類には3,4-デヒドロレチナールが視覚現象に関与しているものがある．森北出版「化学辞典（第2版）

使用Corotenoid component of the visual pigments. All-trans retinal is converted to retinoic acid in vivo by the action of retinal dehydrogenase.

一般的な説明All trans-Retinal is one of the major derivatives of vitamin A group. A variety of food serves as a source of vitamin A. It is predominant in liver and among the brightly colored vegetables.

調製方法 · 1 件

純化方法The aldehyde is separated from retinol by column chromatography on water-deactivated alumina. Elute with 1-2% acetone in hexane, or on TLC plates of silica gel G and using the same eluting solvent. It crystallises from pet ether or n-hexane as yellow-orange crystals, and the UV in hexane has max at 373nm (A1cm 1% 1,548) and 368nm ( 48,000). It is an irritant and is light sensitive. Store it in sealed ampoules under N2. The semicarbazone forms yellow crystals from CHCl3/Et2O or EtOH, m 199-201o(dec). The 9-cis-isomer [514-85-2] and the 13-cis-isomer [472-86-6] [max at 375nm ( 1,250) in EtOH] are also available commercially. [Beilstein 7 III 1742.]