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68-26-8

Basic Information
CAS No.: 68-26-8
Name: VITAMIN A
Article Data: 126
Molecular Structure:
Molecular Structure of 68-26-8 (VITAMIN A)
Formula: C20H30O
Molecular Weight: 286.458
Synonyms: Retinol,all-trans- (8CI);2,4,6,8-Nonatetraen-1-ol, 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-,(all-E)-;A-Mulsal;A-Vi-Pel;Acon;Agiolan;Alcovit A;Alphalin;Anatola;Anti-Infective vitamin;Aoral;Apostavit;Aquasol A Parenteral;Avibon;Avitol;Axerophthol;Biosterol;Disatabs Tabs;Dofsol;Epiteliol;Lard Factor;NSC 122759;Oleovitamin a;Ophthalamin;PlivitA;Retinol 50C;Tegosphere VitA;Thalasphere;Veroftal;Vi-Dom-A;Vitamin Aalcohol, all-trans-;Vitamin A1 alcohol;Vitamin A1, all-trans-;Vitpex;all-trans-Retinol;all-trans-Vitamin A;all-trans-Vitamin A alcohol;trans-VitaminA alcohol;
EINECS: 200-683-7
Density: 0.954 g/cm3
Melting Point: 63.5 ºC
Boiling Point: 421.2 ºC at 760 mmHg
Flash Point: 147.3 ºC
Solubility: Practically insoluble inwaterorglycerol; soluble in absolute alcohol,methanol,℃hloroform, ether, fats and oils.
Appearance: yellow to orange crystalline solid
Hazard Symbols: HarmfulXn,DangerousN,FlammableF
Risk Codes: R22-38-67-65-62-51/53-48/20-11
Safety: 36/37-61-62
Transport Information: UN 1208 3/PG 2
PSA: 20.23000
LogP: 5.51030
Synthetic route
557-75-5

ethenol

39668-33-2

(+/-)-7-hydroxy-3.7-dimethyl-1-(2.2.6-trimethyl-cyclohexen-(6)-yl)-nonatetraene-(1.3.5.8)

68-26-8

RETINOL

Conditions
ConditionsYield
With hydrogenchloride In toluene at 50℃; for 1h; Temperature;95%
50465-60-6

9-(2,6,6-Trimethyl-cyclohex-1-enyl)-5-phenyl-sulphonyl-3,7-dimethyl-1-acetoxy-nona-2,6,8-triene

68-26-8

RETINOL

Conditions
ConditionsYield
With sodium ethanolate In ethanol Heating;94%
3917-41-7

(2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienal

53170-97-1

(E)-4-chloro-3-methyl-2-buten-1-ol

68-26-8

RETINOL

Conditions
ConditionsYield
Stage #1: (E)-4-chloro-3-methyl-2-buten-1-ol With triphenylphosphine In methanol at 45℃; for 1h;
Stage #2: (2E,4E)-3-methyl-5-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4-pentadienal With sodium hydroxide In methanol; water at 45℃; for 1h; Reagent/catalyst;
90%
138922-13-1

tert-Butyl-[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenyloxy]-diphenyl-silane

68-26-8

RETINOL

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride In tetrahydrofuran84%
127-47-9

Retinol acetate

68-26-8

RETINOL

Conditions
ConditionsYield
With methyllithium In tetrahydrofuran at -15℃; for 0.75h; Inert atmosphere;83%
With water
With methyllithium In diethyl ether at -15℃; for 2h;600 mg
120040-83-7

(E,E)-(5-hydroxy-3-methylpenta-1,3-dienyl)boronic acid

138846-06-7

2-[(1’E,3’E)-3’-methyl-4’-iodobuta-1’,3’-dien-1’yl]-1,3,3-trimethylcyclohex-1-ene

68-26-8

RETINOL

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); TlOH In tetrahydrofuran for 0.5h; Ambient temperature;83%
1430344-83-4

(2E,4E)-5-(benzyldimethylsilyl)-3-methylpenta-2,4-dien-1-ol

138846-06-7

2-[(1’E,3’E)-3’-methyl-4’-iodobuta-1’,3’-dien-1’yl]-1,3,3-trimethylcyclohex-1-ene

68-26-8

RETINOL

Conditions
ConditionsYield
Stage #1: (2E,4E)-5-(benzyldimethylsilyl)-3-methylpenta-2,4-dien-1-ol With tetrabutyl ammonium fluoride In tetrahydrofuran at 0℃; for 0.5h; Hiyama Coupling; Inert atmosphere;
Stage #2: 2-[(1’E,3’E)-3’-methyl-4’-iodobuta-1’,3’-dien-1’yl]-1,3,3-trimethylcyclohex-1-ene With tris(dibenzylideneacetone)dipalladium(0) chloroform complex In tetrahydrofuran at 0 - 25℃; for 3.5h; Hiyama Coupling; Inert atmosphere;
82%
Stage #1: (2E,4E)-5-(benzyldimethylsilyl)-3-methylpenta-2,4-dien-1-ol With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 0.5h; Hiyama Coupling; Inert atmosphere; Darkness;
Stage #2: 2-[(1’E,3’E)-3’-methyl-4’-iodobuta-1’,3’-dien-1’yl]-1,3,3-trimethylcyclohex-1-ene With tris(dibenzylideneacetone)dipalladium(0) chloroform complex In tetrahydrofuran for 1h; Hiyama Coupling; Inert atmosphere; Darkness;
77%
118353-70-1

tBDMS-retinol

68-26-8

RETINOL

Conditions
ConditionsYield
With tetrabutyl ammonium fluoride80%
With tetrabutyl ammonium fluoride In tetrahydrofuran for 2h; Ambient temperature;80%
127-47-9

Retinol acetate

57-10-3

1-hexadecylcarboxylic acid

A

79-81-2

retinyl palmitate

B

68-26-8

RETINOL

Conditions
ConditionsYield
With Novozyme 435 (from Candida antarctica immobilized on acrylic resin); Amberlyst A-21 In toluene at 20℃; for 15h; Product distribution / selectivity; Enzymatic reaction;A 78%
B n/a
103905-07-3

1-acetoxy-3,7-dimethyl-8-(tetrahydropyran-2-yl)oxy-9-phenylsulfonyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2(E),6(E)-nonadiene

A

2052-63-3

2-cis-Vitamin-A

C

22737-96-8

11-cis-retinol

D

68-26-8

RETINOL

Conditions
ConditionsYield
With potassium methanolate In cyclohexane at 38℃; for 2h;A n/a
B n/a
C n/a
D 77%
With potassium methanolate In cyclohexane at 38℃; for 2h; Title compound not separated from byproducts;
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Chemistry

The Molecular Structure of Vitamin A (CAS NO.68-26-8):

Empirical Formula: C20H30O
Molecular Weight: 286.4516 
IUPAC Name: (2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraen-1-ol 
Appearance: Yellow-Orange Powder
Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals;Retinoids;Intracellular receptor
Nominal Mass: 286
Average Mass: 286.4516 
Monoisotopic Mass: 286.229666
Index of Refraction: 1.549
Molar Refractivity: 95.49 cm3
Molar Volume: 300 cm3
Surface Tension: 36.6 dyne/cm
Density: 0.954 g/cm3
Flash Point: 147.3 °C
Enthalpy of Vaporization: 77.99 kJ/mol
Boiling Point: 421.2 °C at 760 mmHg
Vapour Pressure: 7.35E-09 mmHg at 25°C 
Stability: Stable, but light and air sensitive. Incompatible with strong acids, strong oxidizing agents
InChI: InChI=1/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+
Smiles: C=1(C(CCCC1C)(C)C)\C=C\C(=C\C=C\C(=C\CO)C)C 
Melting Point: 63.5 °C
log P (octanol-water): 5.68  
Water Solubility: 0.671 mg/L at 25 °C 
Henry's Law Constant: 1.16E-04 atm-m3/mole at 25 °C 
Atmospheric OH Rate Constant: 4.00E-10 cm3/molecule-sec at 25 °C 

History

  Vitamin A (CAS NO.68-26-8) was first synthesized in 1947 by two Dutch chemists, David Adriaan van Dorp and Jozef Ferdinand Arens. The discovery of vitamin A may have stemmed from research dating back to 1906, indicating that factors other than carbohydrates, proteins, and fats were necessary to keep cattle healthy.By 1917 one of these substances was independently discovered by Elmer McCollum at the University of Wisconsin-Madison, and Lafayette Mendel and Thomas Burr Osborne at Yale University. Since "water-soluble factor B" ( Vitamin B ) had recently been discovered, the researchers chose the name "fat-soluble factor A" (vitamin A).

Uses

 Vitamin A (CAS NO.68-26-8) is important in vision and bone growth,and appears to function in maintaining normal skin health.It is used in medicine and feed industry.

Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo oral 912ku/kg/2Y-I (912000iu/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

LIVER: OTHER CHANGES

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"
New England Journal of Medicine. Vol. 294, Pg. 805, 1976.
child TDLo oral 5475ku/kg/1Y- (5475000iu/kg) LUNGS, THORAX, OR RESPIRATION: PLEURAL EFFUSION

GASTROINTESTINAL: OTHER CHANGES

MUSCULOSKELETAL: OTHER CHANGES
Clinical Pediatrics Vol. 21, Pg. 435, 1982.
infant LDLo oral 442ku/kg/11D- (442000iu/kg) BEHAVIORAL: ANOREXIA (HUMAN

BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

KIDNEY, URETER, AND BLADDER: "CHANGES IN TUBULES (INCLUDING ACUTE RENAL FAILURE, ACUTE TUBULAR NECROSIS)"
Archives of Pathology and Laboratory Medicine. Vol. 108, Pg. 838, 1984.
man TDLo oral 1217ku/kg/1Y- (1217000iu/kg) LIVER: "HEPATITIS, FIBROUS (CIRRHOSIS, POST-NECROTIC SCARRING)"

BLOOD: HEMORRHAGE

BLOOD: CHANGES IN SPLEEN
Liver Annual. Vol. 12, Pg. 381, 1992.
mouse LD50 intraperitoneal 1510mg/kg (1510mg/kg)   Journal of the American Academy of Dermatology. Vol. 6, Pg. 652, 1982.
mouse LD50 oral 1510mg/kg (1510mg/kg)   "The Retinoids, Vol.2," Sporn, M.B., et al., eds., New York, Academic Press, Inc., 1984Vol. 2, Pg. 287, 1984.
rat LD50 oral 2gm/kg (2000mg/kg)   Acta Dermato-Venereologica, Supplementum. Vol. 74, Pg. 29, 1975.
women TDLo oral 91000iu/kg/26 (91000iu/kg) BEHAVIORAL: ANOREXIA (HUMAN

LIVER: "JAUNDICE, OTHER OR UNCLASSIFIED"

SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"
American Journal of Medicine. Vol. 97, Pg. 523, 1994.

Consensus Reports

Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Safety Profile

Moderately toxic by ingestion. Human teratogenic effects by ingestion: developmental abnormalities of the craniofacial area and urogenital system. An experimental teratogen. Experimental reproductive effects. Human mutation data reported. When heated to decomposition it emits acrid smoke and irritating fumes.
Hazard Codes: HarmfulXnDangerousNFlammableF
Risk Statements: 22-38-67-65-62-51/53-48/20-11 
R22: Harmful if swallowed
R38: Irritating to skin
R67: Vapours may cause drowsiness and dizziness
R65: Harmful: may cause lung damage if swallowed
R62: Risk of impaired fertility
R51/53: Toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment
R48/20: Harmful: danger of serious damage to health by prolonged exposure through inhalation
R11: Highly flammable
Safety Statements: 36/37-61-62 
S36/37: Wear suitable protective clothing and gloves
S61: Avoid release to the environment. Refer to special instructions / safety data sheets
S62: If swallowed, do not induce vomitting; seek medical advice immediately and show this container or label
RIDADR: UN 1208 3/PG 2
WGK Germany: 3
RTECS: VH6750000
F: 8-10-16-23 
F 8: Photosensitive
F 10: Keep under argon
F 16: Decomposes easily
F 23: Sensitive to air

Specification

 Vitamin A (CAS NO.68-26-8) is also called as Retinol [INN:BAN] ; (all-E)-3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol ; 2,4,6,8-Nonatetraen-1-ol, 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (all-E)- ; 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclchexen-1-yl)-2,4,6,8-nonatetraen-1-ol ; 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraen-1-ol, (all-E)- ; A-Mulsal ; A-Sol ; A-Vi-Pel ; A-Vitan ; ACON ; ATAV ; Afaxin ; Agiolan ; Agoncal ; Alcovit A ; All-trans retinol ; Alphalin ; Alphasterol ; Anatola ; Anatola A ; Anti-infective vitamin ; Antixerophthalmic vitamin ; Antixerophthalmisches Vitamin ; Aoral ; Apexol ; Apostavit ; Aquasol A ; Aquasynth ; Atars ; Avibon ; Avita ; Avitol ; Axerol ; Axerophthol ; Axerophtholum ; BRN 0403040 ; Bentavit A ; Biosterol ; Chocola A ; Del-VI-A ; Disatabs Tabs ; Dofsol ; Dohyfral A ; EINECS 200-683-7 ; Epiteliol ; HI-A-Vita ; HSDB 815 ; Homagenets Aoral ; Lard factor ; Myvpack ; NSC 122759 ; Nio-A-let ; Oleovitamin A ; Ophthalamin ; Plivit A ; Prepalin ; Retinol ; Retinol, all trans- ; Retinolo ; Retinolo [DCIT] ; Retinolum ; Retinolum [INN-Latin] ; Retrovitamin A ; Sehkraft A ; Solu-A ; Super A ; Testavol ; Testavol S ; UNII-81G40H8B0T ; UNII-G2SH0XKK91 ; VI-alpha ; Vaflol ; Vafol ; Veroftal ; Vi-Dom-A ; Vi-alpha ; Vi-alpha; Vi-alpha ; Vio-A ; Vitamin A alcohol (VAN) ; Vitamin A alcohol, all-trans- ; Vitamin A1 ; Vitamin A1 alcohol ; Vitamin A1 alcohol, all trans ; Vitamin A1, all-trans- ; Wachstumsvitamin ; all-trans-Retinol ; all-trans-Retinyl alcohol ; all-trans-Vitamin A ; all-trans-Vitamin A alcohol ; 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonate-traen-1-ol ; Alcohol 9,13-dimethyl-7-(1,1,5-trimethyl-6-cyclohexen-5-yl)-7,9,11,13-nonatetraen-15-ol  .