8,16,25-tris(benzenesulfonyl)-2,6,10,14,19,23,27,31-octamethyl-2,6,10,14,18,22,26,30-dotriacontaoctaene-9,24-diol, bis(tetrahydropyranyl) ether
lycopene
Conditions | Yield |
---|---|
With potassium methanolate In cyclohexane; benzene at 70 - 80℃; for 13h; | 79% |
With potassium methanolate In cyclohexane; benzene at 70 - 80℃; for 13h; Product distribution / selectivity; | 79% |
8,16,25-tris(benzenesulfonyl)-2,6,10,14,19,23,27,31-octamethyl-2,6,10,14,18,22,26,30-dotriacontaoctaene-9,24-diol, bis(tetrahydropyranyl) ether
A
lycopene
B
(9Z)-lycophene
Conditions | Yield |
---|---|
With potassium methanolate In cyclohexane; benzene at 70 - 80℃; for 13h; Inert atmosphere; | A 79% B n/a |
7,7',11,11'-tetra(phenylsulfonyl)-7,7',8,8',11,11',12,12'-octahydrolycopene
A
lycopene
B
(9Z)-lycophene
Conditions | Yield |
---|---|
With sodium ethanolate In ethanol Heating; | A 78% B 20% |
11,11',12,12'-tetrahydro-11,11'-bis(phenylsulfonyl)lycopene
lycopene
Conditions | Yield |
---|---|
With sodium ethanolate In ethanol; benzene at 90℃; for 12h; | 78% |
Conditions | Yield |
---|---|
Stage #1: benzothiazol-2-yl geranyl sulfone With sodium hexamethyldisilazane In tetrahydrofuran at -78℃; for 0.25h; Stage #2: crocetindial In tetrahydrofuran at -78℃; for 1.5h; | 72% |
dodecanedial
3,7,11-trimethyl-1,3,6,10-tetraene-dodecyl diethyl phosphonate
lycopene
Conditions | Yield |
---|---|
Stage #1: 3,7,11-trimethyl-1,3,6,10-tetraene-dodecyl diethyl phosphonate With n-butyllithium In tetrahydrofuran; hexane at -40℃; for 2h; Inert atmosphere; Stage #2: dodecanedial In tetrahydrofuran; hexane at -40 - 30℃; for 1.58333h; | 71% |
2,7-dimethyl-2,4,6-octanetriene-1,8-dialdehyde
3,7,11-trimethyl-1,3,6,10-tetraene-dodecyl diethyl phosphonate
lycopene
Conditions | Yield |
---|---|
Stage #1: 3,7,11-trimethyl-1,3,6,10-tetraene-dodecyl diethyl phosphonate With potassium tert-butylate In tetrahydrofuran; dimethyl sulfoxide at -30 - -25℃; for 5h; Wittig-Horner Reaction; Inert atmosphere; Stage #2: 2,7-dimethyl-2,4,6-octanetriene-1,8-dialdehyde In tetrahydrofuran; dimethyl sulfoxide at -30 - 20℃; for 1.25h; Wittig-Horner Reaction; Inert atmosphere; | 59% |
Stage #1: 3,7,11-trimethyl-1,3,6,10-tetraene-dodecyl diethyl phosphonate With potassium tert-butylate In tetrahydrofuran; dimethyl sulfoxide at 5℃; for 2h; Inert atmosphere; Stage #2: 2,7-dimethyl-2,4,6-octanetriene-1,8-dialdehyde In tetrahydrofuran; dimethyl sulfoxide at 5 - 25℃; for 1.58h; Stage #3: In chloroform for 2h; Reflux; Inert atmosphere; | 52.3% |
Stage #1: 3,7,11-trimethyl-1,3,6,10-tetraene-dodecyl diethyl phosphonate With potassium tert-butylate In tetrahydrofuran; dimethyl sulfoxide at 5℃; for 2h; Inert atmosphere; Stage #2: 2,7-dimethyl-2,4,6-octanetriene-1,8-dialdehyde In tetrahydrofuran; dimethyl sulfoxide at 5 - 25℃; for 1.58333h; | 52.3% |
(3E,5E,7E,9E,11E)-4,8,12,16-tetramethylheptadeca-1,3,5,7,9,11,15-heptaene
lycopene
Conditions | Yield |
---|---|
With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride In dichloromethane at 50℃; for 6.5h; Inert atmosphere; | 58% |
9,24-dibromo-8,16,25-tris(benzenesulfonyl)-2,6,10,14,19,23,27,31-octamethyldotriaconta-2,6,10,14,18,22,26,30-octaene
lycopene
Conditions | Yield |
---|---|
With potassium methanolate In cyclohexane; benzene at 70 - 80℃; for 11h; | 57% |
With potassium methanolate In cyclohexane; benzene at 70 - 80℃; for 11h; Product distribution / selectivity; | 57% |
9,24-dibromo-8,16,25-tris(benzenesulfonyl)-2,6,10,14,19,23,27,31-octamethyldotriaconta-2,6,10,14,18,22,26,30-octaene
A
lycopene
B
(9Z)-lycophene
Conditions | Yield |
---|---|
With potassium methanolate In cyclohexane; benzene at 70 - 80℃; for 11h; Inert atmosphere; | A 57% B n/a |
8,16,25-tris(benzenesulfonyl)-2,6,10,14,19,23,27,31-octamethyl-2,6,10,14,18,22,26,30-dotriacontaoctaene-9,24-diol, bis(methoxymethyl) ether
lycopene
Conditions | Yield |
---|---|
With potassium methanolate In cyclohexane; benzene at 70 - 80℃; for 15h; | 56% |
With potassium methanolate In cyclohexane; benzene at 70 - 80℃; for 15h; Product distribution / selectivity; | 56% |
8,16,25-tris(benzenesulfonyl)-2,6,10,14,19,23,27,31-octamethyl-2,6,10,14,18,22,26,30-dotriacontaoctaene-9,24-diol, bis(methoxymethyl) ether
A
lycopene
B
(9Z)-lycophene
Conditions | Yield |
---|---|
With potassium methanolate In cyclohexane; benzene at 70 - 80℃; for 15h; Inert atmosphere; | A 56% B n/a |
Conditions | Yield |
---|---|
With potassium tert-butylate In tetrahydrofuran; chloroform; benzene | 54% |
8,16,25-tris(benzenesulfonyl)-2,6,10,14,19,23,27,31-octamethyl-2,6,10,14,18,22,26,30-dotriacontaoctaene-9,24-diol, bis(1-ethoxyethyl) ether
lycopene
Conditions | Yield |
---|---|
With potassium methanolate In cyclohexane; benzene at 70 - 80℃; for 18h; | 52% |
With potassium methanolate In cyclohexane; benzene at 70 - 80℃; for 18h; Product distribution / selectivity; | 52% |
8,16,25-tris(benzenesulfonyl)-2,6,10,14,19,23,27,31-octamethyl-2,6,10,14,18,22,26,30-dotriacontaoctaene-9,24-diol, bis(1-ethoxyethyl) ether
A
lycopene
B
(9Z)-lycophene
Conditions | Yield |
---|---|
With potassium methanolate In cyclohexane; benzene at 70 - 80℃; for 18h; Inert atmosphere; | A 52% B n/a |
(1E,3E)-2-[4,8-dimethylnona-1,3,7-trienyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane
(2E,4E,6E,8E,10E,12E,14E)-2,15-diiodo-6,11-dimethylhexadeca-2,4,6,8,10,12,14-heptaene
lycopene
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); thallium(I) hydroxide; 2,6-di-tert-butyl-4-methyl-phenol In tetrahydrofuran; water; toluene at 25℃; for 5h; Suzuki Coupling; Inert atmosphere; | 52% |
C56H80O8S2
lycopene
Conditions | Yield |
---|---|
With potassium methanolate In cyclohexane at 80℃; for 16h; | 28% |
tetrachloromethane
N-Bromosuccinimide
all-trans-neurosporene
acetic acid
lycopene
Conditions | Yield |
---|---|
at 0℃; |
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 4 h / 0 - 25 °C / Molecular sieve; Inert atmosphere 2.1: lithium diisopropyl amide / tetrahydrofuran; hexane / 0.5 h / -78 °C / Inert atmosphere 2.2: 1.5 h / -78 - 25 °C / Inert atmosphere 3.1: zirconocene dichloride; diisobutylaluminium hydride / tetrahydrofuran; hexane / 1 h / 0 - 25 °C / Inert atmosphere 3.2: 0.5 h / -78 °C / Inert atmosphere 4.1: tetrakis(triphenylphosphine) palladium(0); copper(I) thiophene-2-carboxylate; Tetrabutylammoniumsalz der Diphenylphosphinsaeure / N,N-dimethyl-formamide / 0.75 h / 25 °C / Inert atmosphere 5.1: manganese(IV) oxide; sodium carbonate / dichloromethane / 0.5 h / 0 - 25 °C / Inert atmosphere 6.1: sodium hexamethyldisilazane / tetrahydrofuran; hexane / 0.5 h / 25 °C / Inert atmosphere 6.2: 2 h / -78 °C / Inert atmosphere 7.1: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 6.5 h / 50 °C / Inert atmosphere View Scheme | |
Multi-step reaction with 3 steps 1: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / 2 h / 25 °C / Inert atmosphere 2: chromium dichloride; lithium chloride / tetrahydrofuran / 25 °C / Inert atmosphere 3: 2,6-di-tert-butyl-4-methyl-phenol; tetrakis(triphenylphosphine) palladium(0); thallium(I) hydroxide / water; tetrahydrofuran; toluene / 5 h / 25 °C / Inert atmosphere View Scheme | |
With triphenylphosphine hydrochloride; N,N-dimethyl-formamide anschliessend mit 2,6,11,15-Tetramethyl-hexadeca-2t,4t,6t,8t,10t,12t,14t-heptaendial dann mit methanol. Natriummethylat; |
15-cis-lycopene
lycopene
Conditions | Yield |
---|---|
With Petroleum ether at 80 - 100℃; |
lycopene
Conditions | Yield |
---|---|
With diethyl ether; phenyllithium anschliessend Erwaermen mit 2,6,11,15-Tetramethyl-hexadeca-2t,4t,6t,8t,10t,12t,14t-heptaendial in Dichlormethan; |
Conditions | Yield |
---|---|
at 80℃; |
Conditions | Yield |
---|---|
Irradiation; |
(13Z)-lycophene
iodine
benzene
A
lycopene
B
lycopene
Conditions | Yield |
---|---|
at 25℃; |
(13Z)-lycophene
iodine
A
lycopene
B
lycopene
Conditions | Yield |
---|---|
at 20℃; |
lycopene
iodine
benzene
A
(13Z)-lycophene
B
lycopene
Conditions | Yield |
---|---|
di-cis(?)-lycopene; |
lycopene
iodine
A
(13Z)-lycophene
B
lycopene
Conditions | Yield |
---|---|
di-cis(?)-lycopene; |
(13Z)-lycophene
lycopene
Conditions | Yield |
---|---|
With hydrogenchloride; sodium chloride; pepsin; Tween-20 In various solvent(s) at 37℃; Kinetics; | |
Multi-step reaction with 2 steps 1: hexane / 792 h / 20 °C 2: hexane / 792 h / 20 °C View Scheme | |
In ethyl acetate at 20℃; for 1128h; Reactivity; Heating; |
lycopene
A
(2E,4E,6E,8E,10E,12E,14E)-2,7,11,15,19-pentamethylicosa-2,4,6,8,10,12,14,18-octaenal
Conditions | Yield |
---|---|
With potassium permanganate; cetyltrimethylammonim bromide In dichloromethane; water; toluene at 26℃; for 0.5h; | A 10.8% B 7.5% C 19.73% D 13.5% E 23.2% |
tetrachloromethane
N-Bromosuccinimide
lycopene
(3E,3'E)-3,4,3',4'-tetradehydro-ψ,ψ-carotene
lycopene
Conditions | Yield |
---|---|
With potassium permanganate; sodium carbonate; benzene |
Conditions | Yield |
---|---|
With potassium permanganate; sodium carbonate; benzene |
lycopene
(+/-)-5,6-dihydro-ψ,ψ-carotene-5rF,6tF-diol
Conditions | Yield |
---|---|
With chloroform; boron fluoride ether anschliessendes Behandeln mit wasserhaltigem Aceton und Natriumhydrogencarbonat; |
lycopene
(+/-)-5rF,6tF-dimethoxy-5,6-dihydro-ψ,ψ-carotene
Conditions | Yield |
---|---|
With boron fluoride ether anschliessendes Behandeln mit Methanol; |
lycopene
lycopene
Conditions | Yield |
---|---|
With iodine di-cis(?)-lycopene; | |
at 25℃; di-cis(?)-lycopene; | |
Multi-step reaction with 2 steps 1: benzene / bei kurzem Kochen 2: iodine View Scheme | |
In ethyl acetate for 12h; Reflux; |
lycopene
(13Z)-lycophene
Conditions | Yield |
---|---|
With benzene at 20℃; beim Stehenlassen; | |
With benzene at 20℃; beim Stehenlassen; bei Gegenwart von Jod; | |
With benzene bei kurzem Kochen; | |
With hydrogenchloride; sodium chloride; pepsin; Tween-20 In various solvent(s) at 37℃; Kinetics; | |
Sonication; Heating; |
The Lycopene, with the CAS registry number 502-65-8, is also known as Lycopene,all-trans-;Psi,psi-carotene;psi,psi-Carotene.It belongs to the product categories of Natural Plant Extract;Aliphatics;Nutritional Ingredients;Intermediates & Fine Chemicals;Pharmaceuticals;Plant extract;from Blakeslea Trispora. Its EINECS number is 207-949-1.This chemical's molecular formula is C40H56 and molecular weight is 536.88. What's more,Its systematic name is Lycopene. moisture sensitive.when you use it, avoid contact with skin and eyes.The Lycopene is pink Powder, heat sensitive-store at-70 C.Combustible.Incompatible with strong oxidizing agents. And it is Carotenoid antioxidant occurring in ripe fruit, especially in tomatoes.
Physical properties about Riboflavin are: (1)ACD/LogP: 15.19; (2)# of Rule of 5 Violations: 2 ; (3)ACD/LogD (pH 5.5): 15.19; (4)ACD/LogD (pH 7.4): 15.19; (5)ACD/BCF (pH 5.5): 1000000.00; (6)ACD/BCF (pH 7.4): 1000000.00; (7)ACD/KOC (pH 5.5): 10000000.00; (8)ACD/KOC (pH 7.4): 10000000.00; (9)#H bond acceptors: 0; (10)#H bond donors: 0; (11)#Freely Rotating Bonds: 16; (12)Index of Refraction: 1.531; (13)Molar Refractivity: 186.857 cm3; (14)Molar Volume: 604.206 cm3; (15)Surface Tension: 31.0919990539551 dyne/cm; (16)Density: 0.889 g/cm3; (17)Flash Point: 350.736 °C Enthalpy of Vaporization: 93.728 kJ/mol; (18)Boiling Point: 660.905 °C at 760 mmHg; (19)Vapour Pressure: 0 mmHg at 25°C.
The Lycopene may cause damage to health. It is irritating to eyes, respiratory system and skin .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 .
You can still convert the following datas into molecular structure:
(1)SMILES:C(\C=C\C=C(\CC/C=C(\C)C)C)(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/C=C(\C)CC\C=C(/C)C)C)C)C)C;
(2)Std. InChI:InChI=1S/C40H56/c1-33(2)19-13-23-37(7)27-17-31-39(9)29-15-25-35(5)21-11-12-22-36(6)26-16-30-40(10)32-18-28-38(8)24-14-20-34(3)4/h11-12,15-22,25-32H,13-14,23-24H2,1-10H3/b12-11+,25-15+,26-16+,31-17+,32-18+,35-21+,36-22+,37-27+,38-28+,39-29+,40-30+;
(3)Std. InChIKey:OAIJSZIZWZSQBC-GYZMGTAESA-N.
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