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2052-63-3 molecular structure
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(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 and InChIs

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

Cite this record

CBID:48 http://www.chembase.cn/molecule-48.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
vitamin A
α-sol
Brand Name
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
Aquasola
Synonyms
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 ALL trans
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-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
Retinol
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
维生素 A 醇 溶液
视黄醇 溶液
视黄醇
CAS Number
2052-63-3
68-26-8
EC Number
200-683-7
203-777-6
MDL Number
MFCD00079548
MFCD00001552
Beilstein Number
403040
PubChem SID
24890099
46508191
24899336
24899395
24890100
160963511
PubChem CID
1071
445354
CHEBI ID
17336
ATC CODE
S01XA02
D10AD02
V04CB01
R01AX02
A11CA01
CHEMBL
986
Chemspider ID
393012
DrugBank ID
DB00162
KEGG ID
D03365
Unique Ingredient Identifier
81G40H8B0T
Wikipedia Title
Vitamin_A
Retinol

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 16.43577  H Acceptors
H Donor LogD (pH = 5.5) 4.694093 
LogD (pH = 7.4) 4.694093  Log P 4.694093 
Molar Refractivity 97.9234 cm3 Polarizability 36.345623 Å3
Polar Surface Area 20.23 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 6.38  LOG S -4.58 
Solubility (Water) 7.58e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
0.671 mg/L expand Show data source
Chloroform expand Show data source
Methanol expand Show data source
Apperance
Light Yellow to Yellow Solid expand Show data source
yellow to orange crystalline expand Show data source
Melting Point
47-50°C expand Show data source
56-61 °C expand Show data source
61-63 °C(lit.) expand Show data source
61-63°C expand Show data source
Flash Point
-14.8 °F expand Show data source
-26 °C expand Show data source
Absorption Wavelength
ε/326 nm, isopropanol 2700 u/mg expand Show data source
Hydrophobicity(logP)
4.1 expand Show data source
Storage Condition
0°C, Store Under Nitrogen, Protect from light expand Show data source
Amber Vial, -86°C Freezer, Under Inert Atmosphere expand Show data source
RTECS
VH6750000 expand Show data source
European Hazard Symbols
Flammable Flammable (F) expand Show data source
Nature polluting Nature polluting (N) expand Show data source
Irritant Irritant (Xi) expand Show data source
Harmful Harmful (Xn) expand Show data source
UN Number
1208 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
2 expand Show data source
3 expand Show data source
Hazard Class
3 expand Show data source
Packing Group
2 expand Show data source
Risk Statements
11-38-48/20-51/53-62-65-67 expand Show data source
22-38 expand Show data source
38 expand Show data source
R:22 expand Show data source
Safety Statements
22-36/37 expand Show data source
9-16-29-33-36/37-61-62 expand Show data source
S:36/37/39 expand Show data source
GHS Pictograms
GHS02 expand Show data source
GHS07 expand Show data source
GHS08 expand Show data source
GHS09 expand Show data source
GHS Signal Word
Danger expand Show data source
Warning expand Show data source
GHS Hazard statements
H225-H304-H315-H336-H361f-H373-H411 expand Show data source
H302-H315 expand Show data source
H315 expand Show data source
GHS Precautionary statements
P210-P261-P273-P281-P301 + P310-P331 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves expand Show data source
Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter expand Show data source
RID/ADR
UN 1208 3/PG 2 expand Show data source
Storage Temperature
-20°C expand Show data source
2-8°C expand Show data source
Legal Status
General Sales Availability (US) expand Show data source
Pregnancy Category
A (US) expand Show data source
Purity
≥90% (HPLC) expand Show data source
≥95% (HPLC) expand Show data source
≥95.0% (HPLC) expand Show data source
≥97.5% (HPLC) expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Biological Source
synthetic expand Show data source
Shelf Life
(limited shelf life) expand Show data source
Shipped in
dry ice expand Show data source
Product Line
BioXtra expand Show data source
Empirical Formula (Hill Notation)
C20H30O expand Show data source

DETAILS

DETAILS

Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC DrugBank DrugBank MP Biomedicals MP Biomedicals
Sigma Aldrich - R7632 external link
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 - 95144 external link
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 - 95146 external link
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 external link
包装
Sealed ampule
Toronto Research Chemicals - R252000 external link
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
DrugBank - DB00162 external link
Item Information
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
MP Biomedicals - 02190268 external link
All Trans Isomer
Crystalline

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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)
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PATENTS

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