(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol

• ChemBase编号: 48
• 分子式: C20H30O
• 平均质量: 286.4516
• 单一同位素质量: 286.22966558
• SMILES: OC/C=C(/C=C/C=C(/C=C/C1=C(CCCC1(C)C)C)\C)\C
• Canonical SMILES: OC/C=C(/C=C/C=C(/C=C/C1=C(C)CCCC1(C)C)\C)\C
• InChI: InChI=1S/C20H30O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,21H,7,10,14-15H2,1-5H3/b9-6+,12-11+,16-8+,17-13+
• InChIKey: FPIPGXGPPPQFEQ-OVSJKPMPSA-N

名称和登记号

名称

• IUPAC标准名: (2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol; 3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraen-1-ol
• IUPAC传统名: α-sol; vitamin A
• 商标名: Aquasola; A-Mulsal; A-Sol; A-Vi-Pel; A-Vitan; Acon; Afaxin; Agiolan; Agoncal; Alcovit A; Alphalin; Alphasterol; Anatola; Anatola A; Anti-Infective vitamin; Antixerophthalmic vitamin; Aoral; Apexol; Apostavit; Aquasol A; Aquasol A Parenteral; Aquasynth; Atars; Atav; Avibon; Avita; Avitol; Axerol; Axerophthol; Bentavit A; Biosterol; Chocola A; Cylasphere; Del-VI-A; Disatabs Tabs; Dofsol; Dohyfral A; Epiteliol; Hi-A-Vita; Homagenets Aoral; Homagenets aorl; Lard Factor; M.V.C. 9+3; M.V.I. Pediatric; M.V.I.-12; Mvc Plus; Myvpack; Nio-A-Let; Oleovitamin A; Ophthalamin; Plivit A; Prepalin; Retrovitamin A; Ro-a-vit; Sehkraft A; Solu-A; Super A; Testavol; Testavol S; Thalasphere; Vaflol; Vafol; Veroftal; Vi-Alpha; Vi-Dom-A; Vi-a; Vio-A; Vitavel A; Vitpex; Vogan; Vogan-Neu; Vogan-nu; Zineb; Zineb 80; Zinosan N; alin; asterol; tROL
• 别名: 维生素 A 醇 溶液; 视黄醇 溶液; 全反式-3,7-二甲基-9-(2,6,6-三甲基-1-环己烯-1-基)-2,4,6,8-壬四烯-1-醇; 抗干眼醇; 维生素 A 醇; 维生素 A; 维生素 A1; 视黄醇; (all-E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol; A-Mulsal; A-Sol; Alphalin; Alphasterol; Anatola; Avita; Avitol; Axerol; NSC 122759; Vitavel A; Vitpex; Vogan; β-Retinol; all-trans-Retinol; 13-cis-Retinol; Retinol; 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-2,4,6,8-nonatetraen-1-ol; Axerophthol; Vitamin A alcohol solution; Retinol solution; Vitamin A; all-trans-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol; all-trans-retinol; All-trans-Retinyl alcohol; all-trans-Vitamin A; All-trans-Vitamin A alcohol; all-trans-Vitamin A1; beta-Retinol; Retin-11,12-t2-ol (9CI); Retinol; trans-Retinol; trans-Vitamin A alcohol; Vitamin A (Feed); Vitamin A alcohol; Vitamin A Palmitate; Vitamin A Solubilized; Vitamin A1; Vitamin A1 alcohol; Vitamin A cryst; [11,12-3H]-Retinol; Vitamin A; Retinol; RETINOL ALL trans

登记号

• CAS号: 2052-63-3; 68-26-8
• EC号: 200-683-7; 203-777-6
• MDL号: MFCD00001552; MFCD00079548
• Beilstein号: 403040
• PubChem SID: 46508191; 24890099; 160963511; 24899336; 24899395; 24890100
• PubChem CID: 1071; 445354
• CHEBI ID: 17336
• ATC码: D10AD02; V04CB01; S01XA02; R01AX02; A11CA01
• CHEMBL: 986
• Chemspider ID: 393012
• DrugBank ID: DB00162
• KEGG ID: D03365
• 美国药典/FDA物质标识码: 81G40H8B0T
• 维基百科标题: Vitamin_A; Retinol

理论计算性质

JChem

• Acid pKa: 16.43577
• 质子受体: 1
• 质子供体: 1
• LogD (pH = 5.5): 4.694093
• LogD (pH = 7.4): 4.694093
• Log P: 4.694093
• 摩尔折射率: 97.9234 cm^3
• 极化性: 36.345623 Å^3
• 极化表面积: 20.23 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 6.38
• LOG S: -4.58
• 溶解度: 7.58e-03 g/l

分子性质

理化性质

• 溶解度: 0.671 mg/L; Chloroform; Methanol
• 外观: Light Yellow to Yellow Solid; yellow to orange crystalline
• 熔点: 47-50°C; 56-61 °C; 61-63 °C(lit.); 61-63°C
• 闪点: -14.8 °F; -26 °C
• 紫外吸收波长: ε/326 nm, isopropanol 2700 u/mg
• 疏水性(logP): 4.1

安全信息

• 保存条件: 0°C, Store Under Nitrogen, Protect from light; Amber Vial, -86°C Freezer, Under Inert Atmosphere
• RTECS编号: VH6750000
• 欧盟危险性物质标志: 易燃性(Flammable) (F); 环境危害性(Nature polluting) (N); 刺激性(Irritant) (Xi); 有害性(Harmful) (Xn)
• 联合国危险货物编号: 1208
• 德国WGK号: 2; 3
• 联合国危险货物等级: 3
• 联合国危险货物包装类别(PG): 2
• 危险公开号: 11-38-48/20-51/53-62-65-67; 22-38; 38; R:22
• 安全公开号: 22-36/37; 9-16-29-33-36/37-61-62; S:36/37/39
• GHS危险品标识: GHS02; GHS07; GHS08; GHS09
• GHS警示词: Danger; Warning
• GHS危险声明: H225-H304-H315-H336-H361f-H373-H411; H302-H315; H315
• GHS警示性声明: P210-P261-P273-P281-P301 + P310-P331
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves; Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter
• RID/ADR: UN 1208 3/PG 2
• 保存温度: -20°C; 2-8°C

药理学性质

• 法定药品分级: General Sales Availability (US)
• 妊娠期药物分类: A (US)

产品相关信息

• 纯度: ≥90% (HPLC); ≥95% (HPLC); ≥95.0% (HPLC); ≥97.5% (HPLC)
• 生物来源: synthetic
• 有效期: (limited shelf life)
• 运输包装: dry ice
• 产品线: BioXtra
• Empirical Formula (Hill Notation): C20H30O

详细说明

MP Biomedicals - 02190268

All Trans Isomer
Crystalline

DrugBank - DB00162

• Drug Groups: approved; nutraceutical
• Description: Retinol and derivatives of retinol that play an essential role in metabolic functioning of the retina, the growth of and differentiation of epithelial tissue, the growth of bone, reproduction, and the immune response. Dietary vitamin A is derived from a variety of carotenoids found in plants. It is enriched in the liver, egg yolks, and the fat component of dairy products. [PubChem]
• Indication: For the treatment of vitamin A deficiency.
• Pharmacology: Vitamin A is effective for the treatment of Vitamin A deficiency. Vitamin A refers to a group of fat-soluble substances that are structurally related to and possess the biological activity of the parent substance of the group called all-trans retinol or retinol. Vitamin A plays vital roles in vision, epithelial differentiation, growth, reproduction, pattern formation during embryogenesis, bone development, hematopoiesis and brain development. It is also important for the maintenance of the proper functioning of the immune system.
• Toxicity: Acute toxicity (single ingestion of 7 500 RE or 25 000 IU per kg or more): Signs and symptoms may be delayed for 8 to 24 hours and include: increased intracranial pressure, headache, irritability, drowsiness, dizziness, lethargy, vomiting, diarrhea, bulging of fontanels in infants, diplopia, papilledema. Peeling of skin around mouth may be observed from 1 to several days after ingestion and may spread to the rest of the body.; Chronic, excessive ingestion (1 200 RE or 4 000 IU/kg daily for 6 to 15 months) may produce symptoms of pseudotumor cerebri, anorexia, weakness, arthralgias, bone pain, bone demineralization, dry skin, cracked lips, brittle nails, hair loss, splenomegaly, hepatomegaly, hypoplastic anemia, leukopenia, optic neuropathy, and blindness. Increased plasma concentrations of vitamin A occur but do not necessarily correlate with toxicity.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic. Retinol is conjugated with glucuronic acid; the B-glucuronide undergoes enterohepatic circulation and oxidation to retinol and retinoic acid. Retinoic acid undergoes decarboxylation and conjugation with glucuronic acid.
• Absorption: Readily absorbed from the normal gastrointestinal tract
• Half Life: 1.9 hours
• Protein Binding: <5% of circulating vitamin A is bound to lipoproteins in blood in normal condition, but may be up to 65% when hepatic stores are saturated because of excessive intake. When released from liver, vitamin A is bound to retinol-binding protein (RBP). Most vitamin A circulates in the form of retinol bound to RBP.
• References: Roncone DP: Xerophthalmia secondary to alcohol-induced malnutrition. Optometry. 2006 Mar;77(3):124-33. [Pubmed]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Sigma Aldrich - 95144

Unit Definition
1 U corresponds to 1 international U acc. to Ph Eur II, 217 (1983)
Biochem/physiol Actions
Retinal, retinol and retinoic acid are the aldehyde, alcohol and acid forms of vitamin A. The retinoids exist as many geometric isomers due to the unsaturated bonds in the aliphatic chain.Retinol is biological active in a wide range of processes.

Sigma Aldrich - R7632

Biochem/physiol Actions
视黄酸受体 (RAR) 和类视色素 X 受体 (RXR) 的配体，这两种受体作为转录因子调控正常和恶性细胞的生长和分化。
包装
防光玻璃小瓶。
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. R7632.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Sigma Aldrich - 95146

Analysis Note
0.25 mg in 1 mL hexane
Biochem/physiol Actions
Retinal, retinol and retinoic acid are the aldehyde, alcohol and acid forms of vitamin A. The retinoids exist as many geometric isomers due to the unsaturated bonds in the aliphatic chain.Retinol is biological active in a wide range of processes.

Sigma Aldrich - R0271

包装
Sealed ampule

Toronto Research Chemicals - R252000

Occurs preformed only in animals; metabolized from carotenoids, such β-carotene, in the intestinal mucosa. Dietary sources include liver, milk, butter, cheese, eggs and fish liver oils or as carotenois from fruits and vegetables. Stored primarily in the l

参考文献

• Roncone DP: Xerophthalmia secondary to alcohol-induced malnutrition. Optometry. 2006 Mar;77(3):124-33. Pubmed
• Davis, M., et al.: J. Biol. Chem., 15, 167 (1913)
• Crouch, R.K., et al.: Photochem. Photobiol., 64, 613 (1913)