CAS No.302-79-4,Tretinoin Suppliers,MSDS download

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Basic Information

Molecular Structure:
CAS No.:	302-79-4
Name:	Tretinoin
Article Data:	98
Cas Database

Formula:	C₂₀H₂₈O₂
Molecular Weight:	300.441
Synonyms:	(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoate;all-trans-beta-Retinoic acid;Vitamin A acid;Tretinoine (French) (EINECS);Retin A;trans-Retinoic acid;all-trans-Vitamin A1 acid;Acide retinoique (French) (DSL);2,4, 6,8-Nonatetranoic acid, 3,7-dimethyl-9-(2,6, 6-trimethyl-1-cyclohexen-1-yl)-, (2E, 4E, 6E, 8E)-;all-trans-Retinoate;AGN 100335;Vitamin A acid sodium salt;Vitamin A1 acid, all-trans-;ATRA;Retin-A;Vesnaroid;Tretin M;all-(E)-Retinoic acid;Retinoic acid, sodium salt;beta-Retinoic acid;Cordes Vas;Aberel;Tretinoin, all-trans-;Retionic acid;Dermairol;Eudyna;Aknefug;Retinoate;all-trans-Retinoic acid;Retacnyl;Tretinoin (all-trans retinoic acid );Tretinoin USP26;
EINECS:	206-129-0
Density:	1.011 g/cm³
Melting Point:	179-184 °C
Boiling Point:	462.8 °C at 760 mmHg
Flash Point:	350.6 °C
Solubility:	insoluble in water
Appearance:	yellow-orange powder
Hazard Symbols:	T,Xn
Risk Codes:	22-63-38-20/21/22
Safety:	53-26-36/37/39-45-36/37
PSA:	37.30000
LogP:	5.60260

Synthetic route

: 3899-20-5
ethyl (all-E)-retinoate

: 302-79-4
all-trans-retinoic-acid

Conditions

Conditions	Yield
With sodium hydroxide In methanol at 50℃; for 0.5h;	98%
With potassium hydroxide In ethanol	83%
With potassium hydroxide In ethanol at 50℃;	83%
With potassium hydroxide In ethanol for 0.166667h; Heating;	71%

: 68-26-8
RETINOL

: 302-79-4
all-trans-retinoic-acid

Conditions

Conditions	Yield
With tris(triphenylphosphine)ruthenium(II) chloride; oxygen; bis-(3-methyl-1-imidazolyl)ethylene tetrafluoroborate In hexane at 50℃; under 760.051 Torr; for 3h; Reagent/catalyst; Darkness;	90.2%
Multi-step reaction with 2 steps 1: MnO2 / CH2Cl2 / 2 h / Ambient temperature 2: 80 percent / AgO, NaCN / methanol / 18 h / Ambient temperature View Scheme
Multi-step reaction with 2 steps 1: 90 percent / MnO2 / CH2Cl2 / Ambient temperature 2: AgO / CNNa / methanol View Scheme

: 370578-75-9
(6R,7R)-3-[(2E,4E,6E,8E)-3,7-Dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2,4,6,8-tetraenoyloxymethyl]-5,8-dioxo-7-(2-phenoxy-acetylamino)-5λ4-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

A: 302-79-4
all-trans-retinoic-acid

B: (R)-2-[(R)-Carboxy-(2-phenoxy-acetylamino)-methyl]-5-methylene-1-oxo-1,2,5,6-tetrahydro-1λ4-[1,3]thiazine-4-carboxylic acid

Conditions

Conditions	Yield
With β-lactamase from Staphylococcus aureus 95; deuterated phosphate buffer In dimethylsulfoxide-d6 at 25℃; pH=7.2;	A n/a B 86%

: 54168-84-2
trans-β-formyl crotonic acid

: [3-methyl-5-(2,6,6-trimethylcyclohexene-1-yl)-2E,4E-pentadiene]-triphenyl phosphonic chloride

: 302-79-4
all-trans-retinoic-acid

Conditions

Conditions	Yield
Stage #1: trans-β-formyl crotonic acid; [3-methyl-5-(2,6,6-trimethylcyclohexene-1-yl)-2E,4E-pentadiene]-triphenyl phosphonic chloride With potassium hydroxide In isopropyl alcohol at -5 - 0℃; for 2h; Wittig Olefination; Inert atmosphere; Stage #2: With hydrogenchloride; palladium diacetate In isopropyl alcohol at 50℃; pH=7 - 8; pH-value; Reagent/catalyst; Temperature;	85.3%

: 54168-84-2
trans-β-formyl crotonic acid

: 53282-28-3
[(2E,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-2,4-dienyl]triphenylphosphonium chloride

: 302-79-4
all-trans-retinoic-acid

Conditions

Conditions	Yield
Stage #1: trans-β-formyl crotonic acid; [(2E,4E)-3-methyl-5-(2,6,6-trimethylcyclohex-1-en-1-yl)penta-2,4-dienyl]triphenylphosphonium chloride With potassium hydroxide In isopropyl alcohol at -5 - 0℃; for 2h; Wittig Olefination; Inert atmosphere; Stage #2: With hydrogenchloride; palladium diacetate In isopropyl alcohol at 50℃; pH=7-8; Reagent/catalyst; Temperature; pH-value; Inert atmosphere;	85.3%

: 116-31-4
all-trans-Retinal

: 302-79-4
all-trans-retinoic-acid

Conditions

Conditions	Yield
With silver(II) oxide; sodium cyanide In methanol for 18h; Ambient temperature;	80%
With sodium cyanide; silver(l) oxide	80%
With silver(II) oxide; sodium cyanide In methanol Yield given;

: 3899-20-5, 51249-34-4, 59699-82-0, 85354-08-1, 86708-67-0, 86708-68-1, 86708-69-2, 86708-70-5
ethyl retinoate

A: 4759-48-2
13-cis-retinoic acid

B: 302-79-4
all-trans-retinoic-acid

Conditions

Conditions	Yield
With potassium hydroxide In ethanol for 0.5h; Heating; Yield given;	A n/a B 77%
With potassium hydroxide In ethanol for 0.5h; Heating; Yields of byproduct given;	A n/a B 77%

: 220212-06-6
(2E,4E)-5-iodo-3-methylpenta-2,4-dienoic acid

: tributyl[(1E,3E)-2-methyl-4-(2,6,6-trimethylcyclohex-1-enyl)buta-1,3-dienyl]stannane

: 302-79-4
all-trans-retinoic-acid

Conditions

Conditions	Yield
[PdCl2(NCMe)2] In N,N-dimethyl-formamide at 25℃; for 3h; Stille cross-coupling reaction;	73%

: 20013-34-7
acide-2-carboxy-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-enyl)-nona-2E,4E,6E,8E-tetraenoique

: 302-79-4
all-trans-retinoic-acid

Conditions

Conditions	Yield
With pyridine In dichloromethane	67%

: 38987-91-6
5-(2,6,6-trimethyl-cyclohex-1-enyl)-3-methyl-1-phenyl-sulphonyl-penta-2,4-diene

: 19041-16-8
(E)-4-bromo-3-methyl-2-butenoic acid

: 302-79-4
all-trans-retinoic-acid

Conditions

Conditions	Yield
Stage #1: 5-(2,6,6-trimethyl-cyclohex-1-enyl)-3-methyl-1-phenyl-sulphonyl-penta-2,4-diene With potassium tert-butylate In tetrahydrofuran at -20℃; for 0.5h; Stage #2: (E)-4-bromo-3-methyl-2-butenoic acid In tetrahydrofuran at -20 - 60℃; for 4h; Julia olefination;	65%

Raw Materials

777916-02-6

59057-30-6

7069-42-3

74-88-4

75-16-1

14398-42-6

22936-96-5

79-81-2

Downstream Products

3012-76-8

66592-72-1

116-31-4

339-16-2

125780-97-4

302-79-4

432-25-7

94-36-0

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Consensus Reports

Reported in EPA TSCA Inventory. EPA Genetic Toxicology Program.

Specification

The Tretinoin, with the CAS registry number 302-79-4,is also known as 3,7-Dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic acid; all-trans-Retinoic acid; Vitamin A acid. It belongs to the product categories of Intermediates & Fine Chemicals;Retinoids;Intracellular receptor;API.Its EINECS number is 206-129-0. This chemical's molecular formula is C20H28O2 and molecular weight is 300.44. What's more,Its systematic name is Tretinoin.It is a yellow-orange powder which has been used to treat acne and other skin problems, and can be used for the unusual type of acne, psoriasis ichthyosis and abnormal.

Physical properties about Tretinoin are:
(1)ACD/LogP: 6.83; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 5.99; (4)ACD/LogD (pH 7.4): 4.19; (5)ACD/BCF (pH 5.5): 13226.03; (6)ACD/BCF (pH 7.4): 210.25; (7)ACD/KOC (pH 5.5): 17912.95; (8)ACD/KOC (pH 7.4): 284.76; (9)#H bond acceptors: 2; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 5; (12)Index of Refraction: 1.556; (13)Molar Refractivity: 95.527 cm3; (14)Molar Volume: 297.151 cm3; (15)Surface Tension: 39.1399993896484 dyne/cm; (16)Density: 1.011 g/cm3; (17)Flash Point: 350.596 °C; (18)Enthalpy of Vaporization: 79.324 kJ/mol; (19)Boiling Point: 462.801 °C at 760 mmHg; (20)Vapour Pressure: 0 mmHg at 25°C.3. Structure Descriptors of Tretinoin

You can still convert the following datas into molecular structure:
(1)SMILES:O=C(O)\C=C(\C=C\C=C(\C=C\C1=C(\CCCC1(C)C)C)C)C;
(2)Std. InChI:InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8+,16-14+;
(3)Std. InChIKey:SHGAZHPCJJPHSC-YCNIQYBTSA-N.

Safety Information of Tretinoin:
The Tretinoin is harmful by inhalation, in contact with skin and if swallowed and rritating to skin. It is possible risk of harm to the unborn child. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) .When you use it wear suitable protective clothing, gloves and eye/face protection. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. This chemical is danger to the environment Avoid exposure - obtain special instructions before use.

Toxicity of Tretinoin is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	208mg/kg (208mg/kg)		Drugs in Japan Vol. -, Pg. 886, 1995.
mouse	LD50	intravenous	92mg/kg (92mg/kg)		United States Patent Document. Vol. #3878202,
mouse	LD50	oral	1100mg/kg (1100mg/kg)		American Journal of Clinical Nutrition. Vol. 52, Pg. 183, 1990.
mouse	LD50	subcutaneous	253mg/kg (253mg/kg)	BEHAVIORAL: SLEEP LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION	Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 3194, 1973.
rat	LD50	intraperitoneal	96mg/kg (96mg/kg)	SPINAL CORD: OTHER DEGENERATIVE CHANGES BEHAVIORAL: ATAXIA BLOOD: NORMOCYTIC ANEMIA	Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 3194, 1973.
rat	LD50	intravenous	75mg/kg (75mg/kg)		Drugs in Japan Vol. -, Pg. 886, 1995.
rat	LD50	oral	2gm/kg (2000mg/kg)		American Journal of Clinical Nutrition. Vol. 52, Pg. 183, 1990.
rat	LD50	subcutaneous	53mg/kg (53mg/kg)	BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS" LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION	Kiso to Rinsho. Clinical Report. Vol. 7, Pg. 3194, 1973.

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