CAS No.68-26-8,Retinol Suppliers

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Basic Information

Molecular Structure:
CAS No.:	68-26-8
Name:	Retinol
Article Data:	126
Cas Database

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:	Xn,N,F
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With tetrabutyl ammonium fluoride In tetrahydrofuran	84%

: 127-47-9
Retinol acetate

: 68-26-8
RETINOL

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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%

Yield

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

Conditions	Yield
With tetrabutyl ammonium fluoride	80%
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

Conditions	Yield
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

...Expand

: 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

B: 68-26-8, 2052-63-3, 6018-74-2, 17706-49-9, 22737-96-8, 29444-25-5, 34218-73-0, 39815-04-8, 69686-68-6, 69686-69-7, 74743-94-5, 84415-27-0, 84415-28-1, 85354-09-2, 85354-10-5, 93380-02-0, 98462-62-5, 137121-52-9, 22737-97-9
9-cis-retinol

C: 22737-96-8
11-cis-retinol

D: 68-26-8
RETINOL

Conditions

Conditions	Yield
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;

...Expand

Raw Materials

865-33-8

141-75-3

50-00-0

Downstream Products

79-81-2

472-86-6

564-87-4

302-79-4

Total:189 Page 1 of 5 1 2 3 4 5 Next>>

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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: Harmful Xn Dangerous N Flammable F
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 .