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[ CAS No. 502-65-8 ] {[proInfo.proName]}

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Chemical Structure| 502-65-8
Chemical Structure| 502-65-8
Structure of 502-65-8 * Storage: {[proInfo.prStorage]}
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Product Details of [ 502-65-8 ]

CAS No. :502-65-8 MDL No. :MFCD00017350
Formula : C40H56 Boiling Point : -
Linear Structure Formula :- InChI Key :OAIJSZIZWZSQBC-GYZMGTAESA-N
M.W : 536.87 Pubchem ID :446925
Synonyms :
NSC 407322

Calculated chemistry of [ 502-65-8 ]

Physicochemical Properties

Num. heavy atoms : 40
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.35
Num. rotatable bonds : 16
Num. H-bond acceptors : 0.0
Num. H-bond donors : 0.0
Molar Refractivity : 188.23
TPSA : 0.0 Ų

Pharmacokinetics

GI absorption : Low
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : 1.47 cm/s

Lipophilicity

Log Po/w (iLOGP) : 8.57
Log Po/w (XLOGP3) : 15.56
Log Po/w (WLOGP) : 12.94
Log Po/w (MLOGP) : 9.21
Log Po/w (SILICOS-IT) : 13.28
Consensus Log Po/w : 11.91

Druglikeness

Lipinski : 2.0
Ghose : None
Veber : 1.0
Egan : 1.0
Muegge : 3.0
Bioavailability Score : 0.17

Water Solubility

Log S (ESOL) : -11.92
Solubility : 0.0000000007 mg/ml ; 0.0 mol/l
Class : Insoluble
Log S (Ali) : -15.7
Solubility : 0.0 mg/ml ; 2.01e-16 mol/l
Class : Insoluble
Log S (SILICOS-IT) : -6.32
Solubility : 0.000258 mg/ml ; 0.000000481 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 6.21

Safety of [ 502-65-8 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 502-65-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 502-65-8 ]

[ 502-65-8 ] Synthesis Path-Downstream   1~85

  • 1
  • [ 56-23-5 ]
  • [ 128-08-5 ]
  • [ 502-65-8 ]
  • [ 4481-63-4 ]
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  • [ 56-23-5 ]
  • [ 128-08-5 ]
  • [ 502-64-7 ]
  • [ 64-19-7 ]
  • [ 502-65-8 ]
  • 4
  • [ 59092-07-8 ]
  • [ 502-65-8 ]
  • 5
  • [ 502-65-8 ]
  • 6,8'-diapo-carotene-6,8'-dial [ No CAS ]
  • 6
  • [ 502-65-8 ]
  • [ 103957-00-2 ]
  • [ 22255-36-3 ]
  • 8
  • [ 502-65-8 ]
  • [ 124270-73-1 ]
  • 11
  • [ 502-65-8 ]
  • [ 4481-63-4 ]
  • 12
  • [ 502-65-8 ]
  • [ 45316-02-7 ]
  • 13
  • [ 502-65-8 ]
  • [ 34561-05-2 ]
  • 16
  • [ 502-65-8 ]
  • lycopene-5,6-epoxide [ No CAS ]
  • 1,5-epoxyiridanyl-lycopene [ No CAS ]
  • 17
  • [ 502-65-8 ]
  • [ 51599-09-8 ]
  • 1,5-epoxyiridanyl-lycopene [ No CAS ]
  • 1,5-dihydroxyiridanyl-lycopene [ No CAS ]
  • 18
  • [ 502-65-8 ]
  • 8'-Apo-β-caroten-8'-al radical cation [ No CAS ]
  • [ 1107-26-2 ]
  • lycopene radical cation [ No CAS ]
  • 19
  • [ 502-65-8 ]
  • all-trans canthaxanthin radical cation [ No CAS ]
  • [ 514-78-3 ]
  • lycopene radical cation [ No CAS ]
  • 20
  • [ 502-65-8 ]
  • zeaxanthin radical cation [ No CAS ]
  • [ 144-68-3 ]
  • lycopene radical cation [ No CAS ]
  • 21
  • [ 502-65-8 ]
  • lutein radical cation [ No CAS ]
  • [ 7481-64-3 ]
  • lycopene radical cation [ No CAS ]
  • 22
  • [ 502-65-8 ]
  • astaxanthin cation radical [ No CAS ]
  • [ 7542-45-2 ]
  • lycopene radical cation [ No CAS ]
  • 23
  • [ 502-65-8 ]
  • [ 51599-09-8 ]
  • [ 51599-10-1 ]
  • lycopene 5,6;5',6'-diepoxide [ No CAS ]
  • lycopene 1,2;5,6-diepoxide [ No CAS ]
  • 24
  • [ 502-65-8 ]
  • [ 51599-09-8 ]
  • [ 51599-10-1 ]
  • lycopene 1,2;5',6'-diepoxide [ No CAS ]
  • lycopene 1,2;5,6-diepoxide [ No CAS ]
  • 25
  • [ 502-65-8 ]
  • [ 51599-09-8 ]
  • lycopene 1,2;1',2'-diepoxide [ No CAS ]
  • 2,6-cyclolycopene-1,5-epoxide A [ No CAS ]
  • 2,6-cyclolycopene-1,5-diol A [ No CAS ]
  • 26
  • [ 502-65-8 ]
  • [ 51599-09-8 ]
  • 2,6-cyclolycopene-1,5-epoxide B [ No CAS ]
  • 2,6-cyclolycopene-1,5-epoxide A [ No CAS ]
  • 2,6-cyclolycopene-1,5-diol A [ No CAS ]
  • 27
  • [ 502-65-8 ]
  • [ 51599-09-8 ]
  • 2,6-cyclolycopene-1,5-epoxide A [ No CAS ]
  • 1,16-didehydro-2,6-cyclolycopen-5-ol [ No CAS ]
  • 2,6-cyclolycopene-1,5-diol A [ No CAS ]
  • 28
  • [ 502-65-8 ]
  • [ 51599-09-8 ]
  • 2,6-cyclolycopene-1,5-epoxide A [ No CAS ]
  • 2,6-cyclolycopene-1,5-diol B [ No CAS ]
  • 2,6-cyclolycopene-1,5-diol A [ No CAS ]
  • 29
  • [ 502-65-8 ]
  • 2,6-cyclolycopene-1,5-epoxide B [ No CAS ]
  • 2,6-cyclolycopene-1,5-epoxide A [ No CAS ]
  • lycopene 1,6;2,5-diepoxide [ No CAS ]
  • 1,16-didehydro-2,6-cyclolycopen-5-ol [ No CAS ]
  • 2,6-cyclolycopene-1,5-diol B [ No CAS ]
  • 2,6-cyclolycopene-1,5-diol A [ No CAS ]
  • 30
  • [ 502-65-8 ]
  • lycopene 1,6;2,5-diepoxide [ No CAS ]
  • 1,16-didehydro-2,6-cyclolycopen-5-ol [ No CAS ]
  • 2,6-cyclolycopene-1,5-diol B [ No CAS ]
  • 2,6-cyclolycopene-1,5-diol A [ No CAS ]
YieldReaction ConditionsOperation in experiment
Lycopene (11.6 g, all E-content 29%) was charged into a 250 ml three necked round bottomed flask containing 2-propanol (75 ml). To the resulting suspension, 2.9 g of thiourea was added and heated to maintain at 90-95C for 15 hrs. The solvent was distilled at reduced pressure at 55-60C. To the residue methanol (50 ml) was added, stirred at 55-60C for 20 minutes and gradually cooled to 20-25C. The crystalline compound formed was filtered, washed with methanol (20 ml), dried under reduced pressure for 3 hours to obtain all-trans <strong>[502-65-8]lycopene</strong> (9.86 g) having 86.46% all-E-isomer and 6.62% Z-isomer content.
In ethyl acetate; at 76℃; for 168h;Heating / reflux;Reactivity; Example 3 Extraction and Isomerization in Ethyl Acetate52 kg of fresh tomatoes containing 100 ppm of <strong>[502-65-8]lycopene</strong> are chopped and homogenized. Part of the water is distilled off under reduced pressure to obtain 18 kg of tomato concentrate. This is extracted with 36 l of watersaturated ethyl acetate; during extraction, the mixture is kept at room temperature shielded from light and under stirring for 2 hours. The extract is then separated from the tomato concentrate. The above described procedure is repeated twice on such tomato concentrate, totally using 108 l of solvent. The combined extracts are washed in a separatory funnel with 27 l of water. The aqueous phase is then discarded while the organic phase is concentrated under reduced pressure to obtain a suspension with 10% w/v dry residue; the dry residue has a total <strong>[502-65-8]lycopene</strong> content of 9.1% w/w and a Z isomer content of 0.46% w/w. This mixture is refluxed (76 C.) under stirring for 7 days before being concentrated to dryness under reduced pressure.46.8 g of final extract with a total <strong>[502-65-8]lycopene</strong> content of 9% w/w and a Z isomer content of 5.59% w/w are obtained; in particular, the E isomer content is 3.41% w/w and the 13-Z isomer content is 0.16% w/w. The HPLC profile of the extract is reported in the Figure.
In hexane; at 69℃; for 144h;Heating / reflux;Reactivity; Example 4 Extraction and Isomerization in Hexane10 kg of fresh tomatoes containing 140 ppm of <strong>[502-65-8]lycopene</strong> are chopped and homogenized. Part of the water is distilled off under reduced pressure to obtain 2.5 kg of tomato concentrate, which is extracted with 12.5 l of hexane. During extraction, the mixture is kept at room temperature shielded from light and under stirring for 2 hours. The extract is then separated from the tomato concentrate. The above described procedure is repeated once on such tomato concentrate, totally using 25 l of solvent. The extracts are combined and concentrated under reduced pressure to obtain a solution with 10% w/v dry residue; the dry residue has a total <strong>[502-65-8]lycopene</strong> content of 9.1% w/w and a Z isomer content of 0.46% w/w. This mixture is refluxed (69 C.) under stirring for 6 days before being concentrated to dryness under reduced pressure. 16.5 g of final extract with total <strong>[502-65-8]lycopene</strong> content of 9.1% w/w and Z isomer content of 5.62% w/w are obtained; in particular, the E isomer content is 3.38% w/w and the 13-Z isomer content is 0.18% w/w.
In butan-1-ol; at 130℃; for 4h;Reactivity; Example 5 Isomerization in Butanol10 kg of fresh tomatoes containing 90 ppm of <strong>[502-65-8]lycopene</strong> are chopped and homogenized. Part of the water is distilled off under reduced pressure to obtain 3.4 kg of tomato concentrate, which is extracted with 7 l of water-saturated ethyl acetate. During extraction, the mixture is kept at room temperature shielded from light and under stirring for 2 hours. The extract is then separated from the tomato concentrate. The above described procedure is repeated twice on such tomato concentrate, totally using 21 l of solvent. The combined extracts are washed in a separatory funnel with 5.3 l of water. The aqueous phase is then discarded while the organic phase is concentrated to dryness under reduced pressure. The dry residue (9.8 g), which has a total <strong>[502-65-8]lycopene</strong> content of 7.8% w/w and a Z-isomer content of 0.40% w/w, is suspended in 98 ml of n-butanol. The mixture is kept at 130 C. under stirring for 4 hours before being concentrated to dryness under reduced pressure. 9.8 g of final extract with a total <strong>[502-65-8]lycopene</strong> content of 6.35% w/w and a Z-isomer content of 4.50% w/w are obtained; in particular, the E-isomer content is 1.85% w/w and the 13-Z isomer content is 0.47% w/w.

YieldReaction ConditionsOperation in experiment
85% Example 4 157.7 mg (0.17 mmol) of the methoxysulfone (IV) was dissolved in 3 ml of tetrahydrofuran, to which was added 182 mg (2.6 mmol) of potassium methoxide. The mixture was stirred at an ambient temperature for 2 hours and thereafter heated under reflux for 7 hours. The temperature of the reaction mixture was then lowered to an ambient temperature. A small amount of methanol was added to the reaction mixture, which was then purified by silica gel chromatography to obtain lycopene (V) in a yield of 85%.
78% EXAMPLE 10-1: Lycopene In a mixture of ethanol (20 ml) and benzene (5 ml), dissolved was 7,7',11,11'-tetra(phenylsulfonyl)-7,7',8,8',11,11',12,12'-octahydrolycopene (H-1) (682 mg, 0.62 mmol). Sodium ethoxide (NaOEt) (3.35 g, 49.3 mmol) was added thereto under argon atmosphere. The reaction mixture was heated under reflux with vigorous stirring for 12 hours. When the reaction was completed, benzene (50 ml) was added thereto to dissolve the mixture, and the resultant solution was washed with 1M-HCl (10 ml). The combined organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated by evaporation under reduced pressure, and the residue was purified by silica gel column chromatography to obtain lycopene of Chemical Formula 2 (260 mg, 0.48 mmol) (yield: 78%). 1H-NMR: delta 1.61 (s, 6H), 1.68 (s, 6H), 1.82 (s, 6H), 1.96 (s, 12H), 2.11 (br s, 8H), 5.11 (br s, 2H), 5.95 (d, 2H, J=10.8 Hz), 6.18 (d, 2H, J=12.1 Hz), 6.24 (d, 2H, J=14.9 Hz), 6.20~6.30 (m, 2H), 6.35 (d, 2H, J=14.8 Hz), 6.49 (dd, 2H, J=14.9, 10.8 Hz), 6.63 (dd, 2H, J=14.8, 12.1 Hz), 6.55~6.70 (m, 2H). 13C-NMR: delta 12.8, 12.9, 17.0, 17.7, 25.7, 26.7, 40.2, 123.9, 124.8, 125.1, 125.7, 130.1, 131.5, 131.8, 132.6, 135.4, 136.2, 136.5, 137.3, 139.5.
EXAMPLE 8 41.2 g of 3,7,11-trimethyldodeca-2,4,6,10-tetraen-1-yl-triphenylphosphonium chloride (prepared according to Example 1) and 5.4 g of 2,7-dimethyl-2E,4E,6E-octatrienedial were dissolved in 410 ml of methylene chloride. The solution was cooled to -5 C. and treated dropwise within 15 minutes with 25.1 g of sodium methylate solution (containing 4.7 g of sodium methylate in 20.4 g of methanol). The reaction mixture was stirred at -5 C. for 30 minutes, then warmed to 20 C. within 10 minutes and stirred at 20 C. for a further 60 minutes. Subsequently, the reaction mixture was transferred into a separating funnel and washed twice with 300 ml of 1 percent sodium chloride solution each time. The organic phase was concentrated to a volume of 100 ml on a rotary evaporator. Subsequently, the methylene chloride was evaporated under normal pressure and replaced by methanol. The mixture was left to cool and was stored at 5 C. overnight in order to complete the crystallization. The crystallizate was filtered off under suction and washed with 50 ml of methanol. There were thus obtained 18.2 g of lycopene in a purity of 86.1% (according to HPLC with an internal standard).
According to another preferred embodiment, the nutritional supplement is intended for adults over the age of 50 and includes 220 mg calcium and about 110 mg phosphorous. ... Folic Acid, Calcium, Manganese, Lutein and Lycopene
Among the carotenes, mention may in particular be made of: alpha-carotene, beta-carotene, lycopene.
Lycopene Description Lycopene is a red pigment found in fruits and vegetables and is a member of the carotenoid family of chemicals.
obtain filter cake which is a sticky substance with black brown color, and the weight of the filter cake is 6.47g after dryness in vacuum. Condensing tetrahydrofuran in the above mother solution to dryness, 12.0L acetone is added to it. The temperature is raised to 60C and refluxed for 0.5hr. Then the above solution is filtered to get about 12.4g phospholipids cream. Condensing the mother solution to dryness, after adding 30ml absolute alcohol, filtering the solution to obtain the purified natural lycopene crystals, and weight of the crystals is 253.0g after dryness in vacuum. The UV content of lycopene in the crystals is about 56.1 wt.%, the phosphorus content is about 0.5wt.%, the residue on ignition is about 0.02 wt.%. 210g purified lycopene crystals are weighted and after jet grinding, mixed with 968g corn oils under stirring for 1.0hr to obtain the oil suspension of lycopene. Wherein the content of lycopene is 10.0wt.%. The oil suspension has high fluidity and could flow freely at temperature 10C.
Example 25 Recipe to Obtain a Lycopene Delivery Vehicle 30 ml of saturated lycopene alcoholic extract were poured onto 70 g of pure micelle powder, then stirred. The final product had a very pleasant orange colour. Ethanol was evaporated at ambient temperature.

  • 35
  • <3,7-dimethyl-octa-2<i>t</i>(?),6-dienyl>-triphenyl-phosphonium bromide [ No CAS ]
  • [ 502-65-8 ]
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  • [ 59092-07-8 ]
  • petroleum ether [ No CAS ]
  • [ 502-65-8 ]
  • 37
  • [ 502-65-8 ]
  • [ 110-54-3 ]
  • [ 7553-56-2 ]
  • [ 4418-71-7 ]
  • [ 502-65-8 ]
  • 38
  • [ 13018-46-7 ]
  • [ 7553-56-2 ]
  • [ 71-43-2 ]
  • [ 4418-71-7 ]
  • [ 502-65-8 ]
  • 39
  • [ 13018-46-7 ]
  • [ 7553-56-2 ]
  • petroleum ether [ No CAS ]
  • [ 4418-71-7 ]
  • [ 502-65-8 ]
  • 40
  • [ 4418-71-7 ]
  • [ 7553-56-2 ]
  • [ 71-43-2 ]
  • [ 13018-46-7 ]
  • [ 502-65-8 ]
  • 41
  • [ 4418-71-7 ]
  • [ 7553-56-2 ]
  • petroleum ether [ No CAS ]
  • [ 13018-46-7 ]
  • [ 502-65-8 ]
  • 42
  • [ 502-65-8 ]
  • [ 71-43-2 ]
  • KMnO4 [ No CAS ]
  • aqueous sodium carbonate [ No CAS ]
  • 6,8'-diapo-carotene-6,8'-dial [ No CAS ]
  • [ 103957-00-2 ]
  • [ 22255-36-3 ]
  • [ 34561-05-2 ]
  • 43
  • [ 502-65-8 ]
  • H2O2 [ No CAS ]
  • [ 1070-48-0 ]
  • 45
  • [ 359643-76-8 ]
  • [ 502-65-8 ]
  • [ 64727-64-6 ]
  • 46
  • [ 502-65-8 ]
  • [ 7585-39-9 ]
  • C42H70O35*C40H56 [ No CAS ]
  • 47
  • [ 502-65-8 ]
  • [ 10016-20-3 ]
  • C40H56*C36H60O30 [ No CAS ]
  • 48
  • [ 630426-43-6 ]
  • [ 502-65-8 ]
  • 49
  • [ 67-56-1 ]
  • [ 502-65-8 ]
  • (7E,9E,11E,13E,15E,17E,19E,21E,23E,25E)-6,27-Dimethoxy-2,6,10,14,19,23,27,31-octamethyl-dotriaconta-2,7,9,11,13,15,17,19,21,23,25,30-dodecaene [ No CAS ]
  • (2RS,5SR,6RS)-1-methoxy-2,6-cyclolycopene-5-ol [ No CAS ]
  • (2RS,5SR,6RS)-1,5-dimethoxy-2,6-cyclolycopene [ No CAS ]
  • 50
  • [ 870636-74-1 ]
  • [ 502-65-8 ]
  • 51
  • [ 13018-46-7 ]
  • [ 502-65-8 ]
YieldReaction ConditionsOperation in experiment
In ethyl acetate; at 20℃; for 1128h;Heating;Reactivity; Stability of lycopene isomers was investigated both in n-hexane and in a tomato oleoresin isomerized by 4 hour heating in ethyl acetate. For this purpose, pure lycopene isomers were stored for 33 days in n-hexane at room temperature and in the absence of light, and the isomerized tomato oleoresin was kept for 55 days at room temperature in the absence of light. Total lycopene concentration and lycopene isomer profiles were measured at various time intervals during the storage.ResultsStability of Lycopene Isomers in n-HexaneResults of the stability test of pure lycopene isomers during storage in n-hexane at room temperature in the absence of light are reported Table 1. All isomers, i.e. included the all-E isomer, underwent a geometrical isomerization during storage. The 13-Z was the less stable isomer: whereas less than 50% of 5-Z, 9-Z and all-E lycopene were transformed after 33 day storage, more than 80% of 13-Z lycopene was converted into other isomers during this period of time. Also, the transformation pathway was different for the 13-Z lycopene compared to the other Z-isomers: while the 13-Z isomer was mainly converted into the all-E isomer, the 5-Z and 9-Z isomers were principally transformed into other Z-isomers during storage in n-hexane.Stability of Lycopene Isomers in Tomato OleoresinResults of the stability test of lycopene isomers in a tomato oleoresin heated for 48 hours in ethyl acetate are reported in Table 2.
  • 52
  • [ 1116695-27-2 ]
  • [ 502-65-8 ]
YieldReaction ConditionsOperation in experiment
57% With potassium methanolate; In cyclohexane; benzene; at 70 - 80℃; for 11h; Method A: Elimination Reaction from the Compound (M-1); To a stirred suspension of the crude (see Example 5) C40 dibromide compound M-1) (0.31 g, 0.27 mmol) in cyclohexane (10 mL) and benzene (5 mL) was added KOMe (0.58 g, 8.27 mmol). The mixture was heated to 7080 C. for 11 h, cooled to room temperature, and 1 M HCl (20 mL) was carefully added. The reaction mixture was extracted with a 9:1 (v:v) solution (60 mL) of hexane and benzene, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The resulting red solid was diluted with hexane (30 mL) and washed with CH3CN (10 mL×3). The combined CH3CN solution was extracted again with hexanes. The hexane layers were combined and concentrated under reduced pressure to give Lycopene of the Chemical Formula 1 (0.11 g, 0.21 mmol) in 76% crude yield. The crude product was purified by recrystallization from MeOH and THF to provide all-(E)-Lycopene (0.083 g, 0.15 mmol) in 57% yield as a dark red crystal.
57% With potassium methanolate; In cyclohexane; benzene; at 70 - 80℃; for 11h;Product distribution / selectivity; [106] Example 9. Lycopene (Chemical Formula 1) [107] Method A: Elimination reaction from the compound (M-I)[108] To a stirred suspension of the crude (see Example 5) C dibromide compound (M-I)40(0.31 g, 0.27 mmol) in cyclohexane (10 mL) and benzene (5 mL) was added KOMe (0.58 g, 8.27 mmol). The mixture was heated to 70-80 C for H h, cooled to room temperature, and 1 M HCl (20 mL) was carefully added. The reaction mixture was extracted with a 9:1 (v:v) solution (60 mL) of hexane and benzene, dried over anhydrous Na SO , filtered, and concentrated under reduced pressure. The resulting red solid was diluted with hexane (30 mL) and washed with CH CN (10 mL X 3). The combined CH CN solution was extracted again with hexanes. The hexane layers were combined and concentrated under reduced pressure to give Lycopene of the Chemical Formula 1 (0.11 g, 0.21 mmol) in 76% crude yield. The crude product was purified by recrystallization from MeOH and THF to provide all-(E)-Lycopene (0.083 g, 0.15 mmol) in 57% yield as a dark red crystal.
  • 53
  • [ 1116695-25-0 ]
  • [ 502-65-8 ]
YieldReaction ConditionsOperation in experiment
79% With potassium methanolate; In cyclohexane; benzene; at 70 - 80℃; for 13h; Method B: Elimination Reaction from the Compound (M-2); To a stirred suspension of the bis(tetrahydropyranyl)ether (M-2) (0.44 g, 0.38 mmol) in cyclohexane (20 mL) and benzene (10 mL) was added KOMe (0.79 g, 11.3 mmol). The mixture was heated to 7080 C. for 13 h, cooled to room temperature, and 1 M HCl (20 mL) was carefully added. The reaction mixture was extracted with a 9:1 (v:v) solution (40 mL) of hexane and benzene, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The resulting red solid was diluted with hexane (30 mL) and washed with CH3CN (10 mL×3). The combined CH3CN solution was extracted again with hexanes. The hexane layers were combined and concentrated under reduced pressure to give Lycopene of the Chemical Formula 1 (0.20 g, 0.37 mmol) in 97% crude yield. The crude product was purified by recrystallization from MeOH and THF to provide all-(E)-Lycopene (0.16 g, 0.29 mmol) in 79% yield as a dark red crystal.
79% With potassium methanolate; In cyclohexane; benzene; at 70 - 80℃; for 13h;Product distribution / selectivity; Method B: Elimination reaction from the compound (M-2) <n="19"/>[110] To a stirred suspension of the bis(tetrahydropyranyl) ether (M-2) (0.44 g, 0.38 mmol) in cyclohexane (20 mL) and benzene (10 mL) was added KOMe (0.79 g, 11.3 mmol). The mixture was heated to 70-80 C for 13 h, cooled to room temperature, and 1 M HCl (20 mL) was carefully added. The reaction mixture was extracted with a 9:1 (v:v) solution (40 mL) of hexane and benzene, dried over anhydrous Na SO , filtered, and concentrated under reduced pressure. The resulting red solid was diluted with hexane (30 mL) and washed with CH CN (10 mL X 3). The combined CH CN solution was extracted again with hexanes. The hexane layers were combined and concentrated under reduced pressure to give Lycopene of the Chemical Formula 1 (0.20 g, 0.37 mmol) in 97% crude yield. The crude product was purified by recrystallization from MeOH and THF to provide all-(E)-Lycopene (0.16 g, 0.29 mmol) in 79% yield as a dark red crystal.
  • 54
  • [ 1116695-26-1 ]
  • [ 502-65-8 ]
YieldReaction ConditionsOperation in experiment
52% With potassium methanolate; In cyclohexane; benzene; at 70 - 80℃; for 18h; Method C: Elimination Reaction from the Compound (M-3); To a stirred suspension of the bis(1-ethoxyethyl)ether (M-3) (0.70 g, 0.61 mmol) in cyclohexane (20 mL) and benzene (5 mL) was added KOMe (1.28 g, 18.30 mmol). The mixture was heated to 7080 C. for 18 h, cooled to room temperature, and 1 M HCl (25 mL) was carefully added. The reaction mixture was extracted with a 9:1 (v:v) solution (50 mL) of hexane and benzene, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The resulting red solid was diluted with hexane (30 mL) and washed with CH3CN (10 ml×3). The combined CH3CN solution was extracted again with hexanes. The hexane layers were combined and concentrated under reduced pressure to give Lycopene of the Chemical Formula 1 (0.24 g, 0.45 mmol) in 73% crude yield. The crude product was purified by recrystallization from MeOH and THF to provide all-(E)-Lycopene (0.17 g, 0.32 mmol) in 52% yield as a dark red crystal.
52% With potassium methanolate; In cyclohexane; benzene; at 70 - 80℃; for 18h;Product distribution / selectivity; [Ill] Method C: Elimination reaction from the compound (M-3) [112] To a stirred suspension of the bis(l-ethoxyehtyl) ether (M-3) (0.70 g, 0.61 mmol) in cyclohexane (20 mL) and benzene (5 mL) was added KOMe (1.28 g, 18.30 mmol). The mixture was heated to 70-80 C for 18 h, cooled to room temperature, and 1 M HCl (25 mL) was carefully added. The reaction mixture was extracted with a 9:1 (v:v) solution (50 mL) of hexane and benzene, dried over anhydrous Na SO , filtered, and concentrated under reduced pressure. The resulting red solid was diluted with hexane (30 mL) and washed with CH CN (10 mL X 3). The combined CH CN solution was extracted again with hexanes. The hexane layers were combined and concentrated under reduced pressure to give Lycopene of the Chemical Formula 1 (0.24 g, 0.45 mmol) in 73% crude yield. The crude product was purified by recrystallization from MeOH and THF to provide all-(E)-Lycopene (0.17 g, 0.32 mmol) in 52% yield as a dark red crystal.
  • 55
  • [ 1116695-24-9 ]
  • [ 502-65-8 ]
YieldReaction ConditionsOperation in experiment
56% With potassium methanolate; In cyclohexane; benzene; at 70 - 80℃; for 15h; Method D: Elimination Reaction from the Compound (M-4); To a stirred solution of the bis(methoxymethyl)ether (M-4) (1.67 g, 1.54 mmol) in cyclohexane (15 mL) and benzene (25 mL) was added KOMe (3.78 g, 53.9 mmol). The mixture was heated to 7080 C. for 15 h, cooled to room temperature, and 1 M HCl (60 mL) was carefully added. The reaction mixture was extracted with a 9:1 (v:v) solution (60 mL) of hexane and benzene, dried over anhydrous Na2SO4, filtered, and concentrated under reduced pressure. The resulting red solid was diluted with hexane (30 mL) and washed with CH3CN (10 mL×3). The combined CH3CN solution was extracted again with hexanes. The hexane layers were combined and concentrated under reduced pressure to give Lycopene of the Chemical Formula 1 (0.61 g, 1.14 mmol) in 74% crude yield. The crude product was purified by recrystallization from MeOH and THF to provide all-(E)-Lycopene (0.46 g, 0.86 mmol) in 56% yield as a dark red crystal.
56% With potassium methanolate; In cyclohexane; benzene; at 70 - 80℃; for 15h;Product distribution / selectivity; [113] Method D: Elimination reaction from the compound (M-4) [114] To a stirred solution of the bis(methoxymethyl) ether (M-4) (1.67 g, 1.54 mmol) in cyclohexane (15 mL) and benzene (25 mL) was added KOMe (3.78 g, 53.9 mmol). The mixture was heated to 70-80 C for 15 h, cooled to room temperature, and 1 M HCl (60 mL) was carefully added. The reaction mixture was extracted with a 9:1 (v:v) solution (60 mL) of hexane and benzene, dried over anhydrous Na SO , filtered, and concentrated under reduced pressure. The resulting red solid was diluted with hexane (30 mL) and washed with CH CN (10 mL X 3). The combined CH CN solution was extracted again with hexanes. The hexane layers were combined and concentrated under reduced pressure to give Lycopene of the Chemical Formula 1 (0.61 g, 1.14 mmol) in 74% crude yield. The crude product was purified by recrystallization from MeOH and THF to provide all-(E)-Lycopene (0.46 g, 0.86 mmol) in 56% yield as a dark red crystal. <n="20"/>[115] The H NMR spectra of all-(E)-Lycopene, which were prepared according to the above methods A-D, were identical to that of the authentic sample.
  • 56
  • [ 101468-86-4 ]
  • [ 13018-46-7 ]
  • [ 502-65-8 ]
  • [ 64727-64-6 ]
YieldReaction ConditionsOperation in experiment
In ethyl acetate; at 20℃;dark;Reactivity; Stability of lycopene isomers was investigated both in n-hexane and in a tomato oleoresin isomerized by 4 hour heating in ethyl acetate. For this purpose, pure lycopene isomers were stored for 33 days in n-hexane at room temperature and in the absence of light, and the isomerized tomato oleoresin was kept for 55 days at room temperature in the absence of light. Total lycopene concentration and lycopene isomer profiles were measured at various time intervals during the storage.ResultsStability of Lycopene Isomers in n-HexaneResults of the stability test of pure lycopene isomers during storage in n-hexane at room temperature in the absence of light are reported Table 1. All isomers, i.e. included the all-E isomer, underwent a geometrical isomerization during storage. The 13-Z was the less stable isomer: whereas less than 50% of 5-Z, 9-Z and all-E lycopene were transformed after 33 day storage, more than 80% of 13-Z lycopene was converted into other isomers during this period of time. Also, the transformation pathway was different for the 13-Z lycopene compared to the other Z-isomers: while the 13-Z isomer was mainly converted into the all-E isomer, the 5-Z and 9-Z isomers were principally transformed into other Z-isomers during storage in n-hexane.
  • 57
  • [ 64727-64-6 ]
  • [ 13018-46-7 ]
  • [ 502-65-8 ]
  • [ 101468-86-4 ]
YieldReaction ConditionsOperation in experiment
In ethyl acetate; at 20℃;dark;Reactivity; Stability of lycopene isomers was investigated both in n-hexane and in a tomato oleoresin isomerized by 4 hour heating in ethyl acetate. For this purpose, pure lycopene isomers were stored for 33 days in n-hexane at room temperature and in the absence of light, and the isomerized tomato oleoresin was kept for 55 days at room temperature in the absence of light. Total lycopene concentration and lycopene isomer profiles were measured at various time intervals during the storage.ResultsStability of Lycopene Isomers in n-HexaneResults of the stability test of pure lycopene isomers during storage in n-hexane at room temperature in the absence of light are reported Table 1. All isomers, i.e. included the all-E isomer, underwent a geometrical isomerization during storage. The 13-Z was the less stable isomer: whereas less than 50% of 5-Z, 9-Z and all-E lycopene were transformed after 33 day storage, more than 80% of 13-Z lycopene was converted into other isomers during this period of time. Also, the transformation pathway was different for the 13-Z lycopene compared to the other Z-isomers: while the 13-Z isomer was mainly converted into the all-E isomer, the 5-Z and 9-Z isomers were principally transformed into other Z-isomers during storage in n-hexane.
  • 58
  • [ 13018-46-7 ]
  • [ 502-65-8 ]
  • [ 64727-64-6 ]
  • [ 101468-86-4 ]
YieldReaction ConditionsOperation in experiment
In ethyl acetate; at 20℃;dark;Reactivity; Stability of lycopene isomers was investigated both in n-hexane and in a tomato oleoresin isomerized by 4 hour heating in ethyl acetate. For this purpose, pure lycopene isomers were stored for 33 days in n-hexane at room temperature and in the absence of light, and the isomerized tomato oleoresin was kept for 55 days at room temperature in the absence of light. Total lycopene concentration and lycopene isomer profiles were measured at various time intervals during the storage.ResultsStability of Lycopene Isomers in n-HexaneResults of the stability test of pure lycopene isomers during storage in n-hexane at room temperature in the absence of light are reported Table 1. All isomers, i.e. included the all-E isomer, underwent a geometrical isomerization during storage. The 13-Z was the less stable isomer: whereas less than 50% of 5-Z, 9-Z and all-E lycopene were transformed after 33 day storage, more than 80% of 13-Z lycopene was converted into other isomers during this period of time. Also, the transformation pathway was different for the 13-Z lycopene compared to the other Z-isomers: while the 13-Z isomer was mainly converted into the all-E isomer, the 5-Z and 9-Z isomers were principally transformed into other Z-isomers during storage in n-hexane.
  • 60
  • (4E,6E,8E,10E)-3,7,11,15-tetramethylhexadeca-2,4,6,8,10,14-hexadienenitrile [ No CAS ]
  • [ 502-65-8 ]
  • 62
  • [ 251291-83-5 ]
  • [ 502-65-8 ]
  • 63
  • 3,7,11-trimethyl-1-(phenylsulfanyl)dodeca-2,4,6,10-tetraene [ No CAS ]
  • [ 502-65-8 ]
  • 65
  • 4-bromo-3-methylbut-2-enyl phenyl sulfide [ No CAS ]
  • [ 502-65-8 ]
  • 66
  • [ 521275-67-2 ]
  • [ 502-65-8 ]
  • 67
  • 3,7,11-trimethyl-1-(phenylsulfanyl)-5-(phenylsulfonyl)dodeca-2,6,10-triene [ No CAS ]
  • [ 502-65-8 ]
  • 68
  • [ 630426-42-5 ]
  • [ 502-65-8 ]
  • 69
  • [ 521275-68-3 ]
  • [ 502-65-8 ]
  • 77
  • [ 108590-00-7 ]
  • [ 502-65-8 ]
  • 78
  • [ 502-65-8 ]
  • [ 122704-25-0 ]
  • 79
  • [ 502-65-8 ]
  • [ 119571-14-1 ]
  • 80
  • [ 502-65-8 ]
  • [ 124159-56-4 ]
  • 81
  • [ 502-65-8 ]
  • [ 13018-46-7 ]
  • [ 64727-64-6 ]
  • [ 101468-86-4 ]
YieldReaction ConditionsOperation in experiment
at 105℃; for 0.0416667h;Microwave irradiation;Product distribution / selectivity; Example 1: Preparation of a primary composition by microwave treatment; 25 g of lycopen oleoresin manufactured by LycoRed Natural Products Industries, Ltd. in Israel, are subjected to a microwave treatment of 150 sec. at 2.45 GHz at a temperature of about 105C. The primary composition thus obtained is cooled down under nitrogen to prevent carotenoid degradation. The ratio of cis : trans isomer for <strong>[502-65-8]lycopene</strong> is about 65: 35 in the resulting composition.
With iodine; In dichloromethane; at 20℃; for 1.83333h;Photolysis;Product distribution / selectivity; Exemple 3: Preparation of a primary composition by radical reaction 2 g oleoresin (Indena 10% <strong>[502-65-8]lycopene</strong>) in 100 mL CH2C12 are mixed with 116 uL Iodine solution (2.8 mg Iodine in 298 pL CH2C12). The mixture is photoisomerised for lh 50 at room temperature and the solvent removed under reduced pressure. The cis : trans isomer ratio is about 77% after photoisomerisation.
In ethyl acetate; for 1h;Heating / reflux;Product distribution / selectivity; Exemple 2: Preparation of a primary composition by thermal treatment 0.28 g of oleoresin (Indena 10% <strong>[502-65-8]lycopene</strong>) in 30 mL of ethyl acetate is isomerised by heating for lh under reflux in a nitrogen atmosphere and evaporation of the solvent under reduced pressure. The cis : trans isomer ratio is about 35% after heating
In High oleic sunflower oil; at 100℃; for 0.25h;Product distribution / selectivity; Exemple 4: Preparation of a primary composition by thermal reaction 10 g of tomato paste (Thorny) are mixed with 10 g of high oleic sunflower oil (Trisun) at room temperature. The mixture is heated using a plate heater for 15 minutes (final temperature 100 C). The cis : trans isomer ratio equals to 40 % after heating.
In ethyl acetate; at 20℃;dark;Reactivity; Stability of <strong>[502-65-8]lycopene</strong> isomers was investigated both in n-hexane and in a tomato oleoresin isomerized by 4 hour heating in ethyl acetate. For this purpose, pure <strong>[502-65-8]lycopene</strong> isomers were stored for 33 days in n-hexane at room temperature and in the absence of light, and the isomerized tomato oleoresin was kept for 55 days at room temperature in the absence of light. Total <strong>[502-65-8]lycopene</strong> concentration and <strong>[502-65-8]lycopene</strong> isomer profiles were measured at various time intervals during the storage.ResultsStability of Lycopene Isomers in n-HexaneResults of the stability test of pure <strong>[502-65-8]lycopene</strong> isomers during storage in n-hexane at room temperature in the absence of light are reported Table 1. All isomers, i.e. included the all-E isomer, underwent a geometrical isomerization during storage. The 13-Z was the less stable isomer: whereas less than 50% of 5-Z, 9-Z and all-E <strong>[502-65-8]lycopene</strong> were transformed after 33 day storage, more than 80% of 13-Z <strong>[502-65-8]lycopene</strong> was converted into other isomers during this period of time. Also, the transformation pathway was different for the 13-Z <strong>[502-65-8]lycopene</strong> compared to the other Z-isomers: while the 13-Z isomer was mainly converted into the all-E isomer, the 5-Z and 9-Z isomers were principally transformed into other Z-isomers during storage in n-hexane.
Tonsil Optimum; In acetic anhydride; at 20℃; for 2h; Example 6 Isomerization on Solid CatalystsMaterialsLycopene-rich tomato oleoresin has been obtained from Indena s.p.a. (Milan, Italy). Its total <strong>[502-65-8]lycopene</strong> content amounted to 9.1%, of which the all-E and the 5-Z isomers represented 93.5% and 6.5%, respectively.MethodsA suspension of tomato oleoresin in acetyl acetate (1:100 w/w) was filtered and incubated with 5% of solid catalyst under constant stirring at room temperature for 2 h. The mixture was centrifuged at maximum speed in an Eppendorf Lab centrifuge.and an aliquot of supernatant evaporated under N2 and re-suspended in n-hexane/BHT.Lycopene AnalysisAmount of total <strong>[502-65-8]lycopene</strong> and <strong>[502-65-8]lycopene</strong> isomer profiles were determined by reverse phase and normal phase HPLC, respectively, under the analytical conditions described in example 1.ResultsLycopene isomer profiles measured in tomato oleoresin isomerised for 2 h at room temperature using solid catalysts are reported in Table 4.Lycopene was efficiently isomerised during 2 h reaction in ethyl acetate at room temperature in the presence of either Tonsil Optimum or Amberlyst 15. With both catalysts a large fraction of <strong>[502-65-8]lycopene</strong> all-E isomer was converted into Z-isomers. Among the identified <strong>[502-65-8]lycopene</strong> isomers, the 5-Z was majoritairement formed, followed by the 9-Z and the 13-Z, respectively; thus, concentration of the 13-Z isomer was, thus, below 10% in the isomerised tomato oleoresins
Amberlyst 15; In acetic anhydride; at 20℃; for 2h; Example 6 Isomerization on Solid CatalystsMaterialsLycopene-rich tomato oleoresin has been obtained from Indena s.p.a. (Milan, Italy). Its total <strong>[502-65-8]lycopene</strong> content amounted to 9.1%, of which the all-E and the 5-Z isomers represented 93.5% and 6.5%, respectively.MethodsA suspension of tomato oleoresin in acetyl acetate (1:100 w/w) was filtered and incubated with 5% of solid catalyst under constant stirring at room temperature for 2 h. The mixture was centrifuged at maximum speed in an Eppendorf Lab centrifuge.and an aliquot of supernatant evaporated under N2 and re-suspended in n-hexane/BHT.Lycopene AnalysisAmount of total <strong>[502-65-8]lycopene</strong> and <strong>[502-65-8]lycopene</strong> isomer profiles were determined by reverse phase and normal phase HPLC, respectively, under the analytical conditions described in example 1.ResultsLycopene isomer profiles measured in tomato oleoresin isomerised for 2 h at room temperature using solid catalysts are reported in Table 4.Lycopene was efficiently isomerised during 2 h reaction in ethyl acetate at room temperature in the presence of either Tonsil Optimum or Amberlyst 15. With both catalysts a large fraction of <strong>[502-65-8]lycopene</strong> all-E isomer was converted into Z-isomers. Among the identified <strong>[502-65-8]lycopene</strong> isomers, the 5-Z was majoritairement formed, followed by the 9-Z and the 13-Z, respectively; thus, concentration of the 13-Z isomer was, thus, below 10% in the isomerised tomato oleoresins

  • 82
  • florisil [ No CAS ]
  • aqueous sodium chloride [ No CAS ]
  • 3,7,11-trimethyl-2,4,6,10-dodecatetraenylphosphonic acid, diethyl ester [ No CAS ]
  • [ 5056-17-7 ]
  • [ 502-65-8 ]
YieldReaction ConditionsOperation in experiment
54% With potassium tert-butylate; In tetrahydrofuran; chloroform; benzene; EXAMPLE VIII Preparation of Lycopene To a solution of 211 mg (0.62 mmole) of 3,7,11-trimethyl-2,4,6,10-dodecatetraenylphosphonic acid, diethyl ester (produced in accordance with Example V) and 40 mg (0.24 mmole) of 2,7-dimethyl-2,4,6-octatrienedial (prepared as described in Example XIV of U.S. Pat. No. 5,061,819) in 2.25 mL of 8:1 (v/v) anhydrous tetrahydrofuran:dimethyl sulfoxide, protected from atmospheric moisture and maintained at a temperature of approximately 50 C. by use of an external ice water bath was added 70 mg (0.62 mmole) of potassium tert-butoxide. This mixture was subsequently stirred in the cold for 15 minutes and then at room temperature for 3 hours. The product was isolated by dilution of the mixture with 25 mL of chloroform and subsequent washing of the organic layer with 5% (w/v) aqueous sodium chloride (3*25 mL). The organic layer was then dried over anhydrous magnesium sulfate and filtered. Removal of the volatile organic solvents by evaporation at reduced pressure, followed by filtration through a small column of Florisil (10 mL, 60-100 mesh, elution with 90 mL of benzene) to remove any unreacted starting materials afforded 70 mg (54% yield) of lycopene, the identity of which was confirmed by proton NMR analysis (recorded in CDCl3 solution at 300 MHz). The latter spectrum exhibited absorptions at delta 5.106, 5.949, 6.198, 6.266, 6.341, 6.493, 6.627, and 6.674 (due to the vinyl H's) and broad singlets at delta 1.960, 1.817, 1.686, and 1.615 (ascribed to the vinyl methyl groups in lycopene). The latter data is fully consistent with that reported for lycopene in an article by U. Hengartner, et al., Helv. Chim. Acta, 75, 1848-1865 (1992) [see Column 1 in Table 2 on page 1854 of that article].
YieldReaction ConditionsOperation in experiment
1,068,709, by reaction with triphenylphosphine and sulfuric acid. Melting point 150 - 155 C. 8 g of this triphenylphosphonium bisulfate are dissolved in 70 ml of water; 30 ml of 30 percent strength by weight hydrogen peroxide are added and 10 percent strength by weight aqueous sodium carbonate solution is then added dropwise whilst stirring. The temperature rises to +30 C. The mixture is then stirred for three hours at room temperature. The precipitated triphenylphosphine oxide and the lycopene are filtered off and washed with warm water. The residue is suspended in ethanol, the suspension is stirred at room temperature and the product is filtered off.
  • 84
  • [ 1116695-24-9 ]
  • [ 502-65-8 ]
  • [ 64727-64-6 ]
  • 85
  • [ 1116695-25-0 ]
  • [ 502-65-8 ]
  • [ 64727-64-6 ]
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