(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 ID: 48
• Molecular Formular: C20H30O
• Molecular Mass: 286.4516
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (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 Traditional name: α-sol; vitamin A
• Brand Name: 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
• Synonyms: (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; 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

Database IDs

• CAS Number: 68-26-8; 2052-63-3
• EC Number: 200-683-7; 203-777-6
• MDL Number: MFCD00079548; MFCD00001552
• Beilstein Number: 403040
• PubChem SID: 46508191; 24890099; 160963511; 24899336; 24899395; 24890100
• PubChem CID: 1071; 445354
• CHEBI ID: 17336
• ATC CODE: S01XA02; D10AD02; A11CA01; R01AX02; V04CB01
• CHEMBL: 986
• Chemspider ID: 393012
• DrugBank ID: DB00162
• KEGG ID: D03365
• Unique Ingredient Identifier: 81G40H8B0T
• Wikipedia Title: Retinol; Vitamin_A

CALCULATED PROPERTIES

JChem

• Acid pKa: 16.43577
• H Acceptors: 1
• H Donor: 1
• LogD (pH = 5.5): 4.694093
• LogD (pH = 7.4): 4.694093
• Log P: 4.694093
• Molar Refractivity: 97.9234 cm^3
• Polarizability: 36.345623 Å^3
• Polar Surface Area: 20.23 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 6.38
• LOG S: -4.58
• Solubility (Water): 7.58e-03 g/l

PROPERTIES

Physical Property

• Solubility: 0.671 mg/L; Chloroform; Methanol
• Apperance: Light Yellow to Yellow Solid; yellow to orange crystalline
• Melting Point: 47-50°C; 56-61 °C; 61-63 °C(lit.); 61-63°C
• Flash Point: -14.8 °F; -26 °C
• Absorption Wavelength: ε/326 nm, isopropanol 2700 u/mg
• Hydrophobicity(logP): 4.1

Safety Information

• Storage Condition: 0°C, Store Under Nitrogen, Protect from light; Amber Vial, -86°C Freezer, Under Inert Atmosphere
• RTECS: VH6750000
• European Hazard Symbols: Flammable (F); Nature polluting (N); Irritant (Xi); Harmful (Xn)
• UN Number: 1208
• German water hazard class: 2; 3
• Hazard Class: 3
• Packing Group: 2
• Risk Statements: 11-38-48/20-51/53-62-65-67; 22-38; 38; R:22
• Safety Statements: 22-36/37; 9-16-29-33-36/37-61-62; S:36/37/39
• GHS Pictograms: GHS02; GHS07; GHS08; GHS09
• GHS Signal Word: Danger; Warning
• GHS Hazard statements: H225-H304-H315-H336-H361f-H373-H411; H302-H315; H315
• GHS Precautionary statements: P210-P261-P273-P281-P301 + P310-P331
• Personal Protective Equipment: 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
• Storage Temperature: -20°C; 2-8°C

Pharmacology Properties

• Legal Status: General Sales Availability (US)
• Pregnancy Category: A (US)

Product Information

• Purity: ≥90% (HPLC); ≥95% (HPLC); ≥95.0% (HPLC); ≥97.5% (HPLC)
• Biological Source: synthetic
• Shelf Life: (limited shelf life)
• Shipped in: dry ice
• Product Line: BioXtra
• Empirical Formula (Hill Notation): C20H30O

DETAILS

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

REFERENCES

• 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)