502-65-8 Usage
Uses
Used in Food Industry:
Lycopene is used as a natural colorant for various food products, providing similar color shades, ranging from yellow to red, as do the natural and synthetic lycopenes. It is used in baked goods, breakfast cereals, dairy products, frozen dairy desserts, dairy product analogues, spreads, bottled water, carbonated beverages, fruit and vegetable juices, soybean beverages, candy, soups, salad dressings, and other foods and beverages.
Lycopene is also used as a food/dietary supplement in products where the presence of lycopene provides a specific value, such as antioxidant or other claimed health benefits.
Used in Pharmaceutical and Research Applications:
Lycopene has been used in high-performance liquid chromatography (HPLC) to determine its concentration in liver, kidney, and lung tissue. It has also been used to induce urokinase plasminogen activator receptor (uPAR) in a prostate cancer cell line and in Raman chemical imaging systems to detect and visualize its internal distribution.
Lycopene has been studied for its potential to prevent carcinogenesis, cardiovascular diseases, and aging due to its antioxidant properties and its strong correlation with the antioxidant capacity of tomatoes.
Production Methods
Lycopene extract from tomato is produced from a tomato variety with high lycopene content, within the range of 150 to 250 mg/kg. This particular variety is not generally marketed for direct consumption, but is used primarily in the production of this lycopene extract. The extract is produced by crushing tomatoes into crude tomato juice that is then separated into serum and pulp. The tomato pulp is then extracted with ethyl acetate. The final product is obtained after solvent removal by evaporation under vacuum at 40-60°C.
Biological Activity
Lycopene may act as an inhibitor of tumor cells. In one study, lycopene was shown to inhibit PDGF-BB-induced signalling and cell migration in human cultured skin fibroblasts (Wu et al., 2007). Trapping of PDGF by lycopene compromised melanoma-induced fibroblast migration and attenuated signalling transduction in fibroblasts (Wu et al., 2007). In functional studies, lycopene inhibited melanoma-induced fibroblast migration in a noncontact coculture system and attenuated signalling in fibroblasts simulated by melanoma-derived conditioned medium (Chiang et al., 2007).
Biochem/physiol Actions
Antioxidant micronutrient of tomatoes associated with decreased risk for cancer and cardiovascular disease. Enhances gap juction communication between cells via upregulation of connexin 43 and reduces proliferation of cancer cells in culture. Inhibits cholesterol synthesis and enhances low-density lipoprotein degradation.
Mechanism of action
Lycopene is a red carotenoid compound found in pink grapefruit, papaya, wolfberry, goji, and tomatoes Dietary supplementation with tomato-based products appears to lower biomarkers of
oxidative stress and carcinogenesis. Limited available evidence from small human intervention studies
indicate that lycopene supplementation for 10–12 weeks may decrease UV-induced erythema. Although
the bioavailability of lycopene in raw tomatoes is low due to tight binding with indigestible fiber, lycopene can be released from the food matrix through heating and food processing.
The effect of topical lycopene is not well characterized. An in vivo study using SKH-1 hairless mice
found that topical lycopene reduced the activity of ornithine decarboxylase (ODC) and myeloperoxidase
(MPO), enzymes that have been implicated in the carcinogenic and acute inflammatory effect of UVB
irradiation.
Mechanism of action
The biological activities of carotenoids such as βcarotene are related in general to their ability to form vitamin A within the body.Since lycopene lacks the β-ionone ring structure, it cannot form vitamin A.Its biological effects in humans have therefore been attributed to mechanisms other than vitamin A. Two major hypotheses have been proposed to explain the anticarcinogenic and antiatherogenic activities of lycopene: nonoxidative and oxidative mechanisms.
Among the nonoxidative mechanisms, the anticarcinogenic effects of lycopene have been suggested to be due to regulation of gap-junction communication in mouse embryo fibroblast cells.Lycopene is hypothesized to suppress carcinogen-induced phosphorylation of regulatory proteins such as p53 and Rb antioncogenes and stop cell division at the G0–G1 cell cycle phase.Astorg and colleagues proposed that lycopene-induced modulation of the liver metabolizing enzyme, cytochrome P4502E1, was the underlying mechanism of protection against carcinogen-induced preneoplastic lesions in the rat liver. Preliminary in vitro evidence also indicates that lycopene reduces cellular proliferation induced by insulin-like growth factors, which are potent mitogens, in various cancer cell lines.Regulation of intrathymic T-cell differentiation (immunomodulation) was suggested to be the mechanism for suppression of mammary tumour growth by lycopene treatments in SHN retired mice.Lycopene also has been shown to act as a hypocholesterolemic agent by inhibiting HMG–CoA (3-hydroxy-3-methylglutaryl–coenzyme A) reductase.
Lycopene has been hypothesized to prevent carcinogenesis and atherogenesis by protecting critical cellular biomolecules, including lipids, lipoproteins, proteins and DNA.In healthy human subjects, lycopene- or tomatofree diets resulted in loss of lycopene and increased lipid oxidation,whereas dietary supplementation with lycopene for 1 week increased serum lycopene levels and reduced endogenous levels of oxidation of lipids, proteins, lipoproteins and DNA.Patients with prostate cancer were found to have low levels of lycopene and high levels of oxidation of serum lipids and proteins.
Anticancer Research
Lycopene is a naturally occurring chemical that manifests as a red pigment contained in common foods such as tomatoes, pink grapefruits, guava, and watermelon (Giovannucci 1999). This is a very strong antioxidant that has been found to prevent and even reverse the progression of prostate cancer, as well as treating benign prostatic hyperplasia. In a recent study, 30 mg a day of lycopene showed curative results in prostate cancer. For best results, supplements are recommended alongside eating and drinking plenty of lycopene-containing food and juices (Jatoi et al. 2007). Earlier research showed that taking a specific combination of lycopene, selenium, and saw palmetto by mouth for 8 weeks reduced pain in men with prostate swelling and pelvic pain more significantly than saw palmetto alone (Feifer et al. 2002).Lycopene shows anticancer activity against prostate, endometrial, breast, and colon carcinomas. It inhibits human cancer cell proliferation by activation of cancer-preventive enzymes like phase II detoxification enzymes, by suppression of insulin-like growth factor-I-stimulated growth (Wang et al. 2012). It also activates antioxidant enzymes like GST, GSH, and GPx and protects from oxidative stress caused by carcinogens. It alters PI3K/AKT pathway and ERK and Bcl-2 signaling in pancreatic and gastric carcinoma cells, respectively (Singh et al. 2016b).
Purification Methods
Crystallise lycopene from CS2/MeOH, diethyl ether/pet ether, or acetone/pet ether. Also purify it by column chromatography on deactivated alumina, CaCO3, calcium hydroxide or magnesia. It is oxygen sensitive and is stored in the dark, in an inert atmosphere. Also purified like -Carotene. [Beilstein 1 III 1076, 1 IV 1165.]
Check Digit Verification of cas no
The CAS Registry Mumber 502-65-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 5,0 and 2 respectively; the second part has 2 digits, 6 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 502-65:
(5*5)+(4*0)+(3*2)+(2*6)+(1*5)=48
48 % 10 = 8
So 502-65-8 is a valid CAS Registry Number.
InChI:InChI=1/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+
502-65-8Relevant articles and documents
A novel and practical synthetic route for the total synthesis of lycopene
Shen, Runpu,Jiang, Xiaoyue,Ye, Weidong,Song, Xiaohua,Liu, Luo,Lao, Xuejun,Wu, Chunlei
, p. 5610 - 5614 (2011)
A novel route for the total synthesis of lycopene 1 is described. The synthesis is based on: (i) a condensation between 4,4-dimethoxy-3-methylbutanal 4 and methylenebisphosphonic acid tetraethyl ester 5, leading to the C6-phosphonate 6, followed by (ii) a modified Wittig-Horner reaction between 6 and 6-methyl-5-hepten-2-one 7 producing dimethoxy-3,5,9-triene 8, and (iii) another modified Wittig-Horner reaction between C15-phosphonate 2 and C10-triene dialdehyde 3 producing all-E-lycopene. The synthetic steps are easily operated and practical for the large-scale production.
Kinetic studies of lycopene isomerization in a tributyrin model system at gastric pH
Moraru, Catalin,Lee, Tung-Ching
, p. 8997 - 9004 (2005)
A semi-preparative HPLC method was developed in order to isolate and purify the 13-cis-lycopene isomer in tomato-based materials. The result was compared with the naturally predominant all-trans-lycopene isomer, in terms of stability to gastric pH at physiological temperature in a tributyrin model system. Kinetic experiments confirmed that lycopene isomerization is a reversible reaction, and under these conditions the all-trans isomer is more stable than the 13-cis isomer. In addition, it was found that at gastric pH 13-cis-lycopene would predominantly isomerize to the all-trans form rather than undergo oxidation/breakdown. A simulation based on the rate constants calculated in the kinetic study indicated that at gastric pH the lycopene isomeric distribution aimed toward an equilibrium characterized by approx 16% 13-cis-, 16% 9-cis-, and 68% all-trans-lycopene. This study suggests that pH-driven isomerization in the stomach is at least partially responsible for the relatively high cis-lycopene proportion found in vivo.
Method for preparing lycopene
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Paragraph 0047-0051; 0053-0056; 0058-0061, (2017/12/30)
The invention discloses a method for preparing lycopene. According to the method, a target product, i.e., the lycopene can be obtained through subjecting 3,7-dimethyl-1,6-octadiene-diethyl phosphate and 2,6,11,15-tetramethyl-2,4,6,8,10,12,14-hexadeca-carbon heptaene dialdehyde, which serve as raw materials, to two step reactions, i.e., a rearrangement dissociation reaction and a condensation reaction only. According to the method, the trans-form content is high, isomerization is not required to be carried out, the route is simple, the operation is simple, the source of the raw materials is convenient, the cost is low, and the recovery rate is high, so that the method is applicable to large-batch industrial production.
METHODS FOR PREPARATION OF LYCOPENES FROM C15-WITTIG SALTS AND METHODS FOR PURIFICATION OF HIGH ALL-E CONTAINING AND HIGH 6Z CONTAINING C15-WITTIG SALTS
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Paragraph 0027, (2016/02/10)
The present invention relates to methods for preparation of lycopenes, especially to lycopenes with high all-E contents or high 6Z contents from C15-Wittig slats mixtures. (with high all-E-contents and high 6Z-contents, respectively). C15-Wittig slats mixtures are purified and 6Z-C15-Wittig salts are extracted from the mixtures. The extracted 6Z-C15-Wittig salts are, used in the synthesis of lycopenes with high 6Z contents and the residues are used in the synthesis of lycopenes with high All-E contents.
Method for preparing lycopene
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, (2017/05/03)
The invention provides a method for preparing lycopene. The method comprises the following steps: under alkaline condition, pseudoionone and methyl chloroacetate are subjected to a reaction to obtain epoxide, then the epoxide is subjected to hydrolysis and decarboxylation under acidic condition to obtain 2,6,10-trimethyl-3,5,9-undecatriene-1-aldehyde; 2,6,10-trimethyl-3,5,9-undecatriene-1-aldehyde and tetraethyl methylenediphosphonate are subjected to a condensation reaction to obtain 3,7,11-trimethyl-1,4,6,10-tetraene dodecyl dialkyl phosphate; 3,7,11-trimethyl-1,4,6,10-tetraene dodecyl dialkyl phosphate is subjected to transposition, and then is subjected to a Wittig-Horner condensation reaction with 2,7-dimethyl-2,4,6-dimethyl-1,8-dialdehyde to obtain lycopene. The preparation method has the advantages of easy acquisition of the raw materials, short synthesis route, and low cost, and is suitable for industrial production.
Stable and bioavailable compositions of isomers of carotenoids for skin and hair
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, (2015/09/28)
Compositions that provide health benefits and methods regarding same are presented. In an embodiment, the present invention provides a primary composition comprising at least one carotenoid-containing material, enriched in Z isomers of the carotenoid compound. For example, the carotenoid-containing material contains by weight a greater percentage of an isomer selected from the group consisting of 5-Z, 9-Z and combinations thereof than of 13-Z isomer.
C5 BENZOTHIAZOLYL SULFONE COMPOUND, METHOD OF PREPARING THE SAME, METHOD OF PREPARING POLYENE DIALDEHYDE COMPOUND USING THE SAME, AND METHOD OF SYNTHESIZING LYCOPENE USING THE SAME
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Paragraph 0062; 0063; 0064, (2016/03/04)
Disclosed are a novel C5 benzothiazolyl sulfone compound having an acetal protecting group, a method of preparing the same, and a method of efficiently preparing an apo-carotene dialdehyde compound having a polyene dialdehyde structure using the same. Also, a method of efficiently preparing lycopene by olefination (Julia-Kocienski) between the apo-carotene dialdehyde compound (C20 crocetin dialdehyde) and C10 benzothiazolyl geranyl sulfone is provided.
Whey protein vehicle for active agent delivery
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, (2015/12/14)
The present invention relates to whey protein micelles, a process for the preparation of aggregates of the sane and particularly to their use as a delivery vehicle for active agents in the field of nutrition or cosmetics.
Methods for preparation of lycopenes from C-15 Wittig salts and methods for purification of high all-E containing and high 6Z containing C15-Wittig salts
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, (2016/01/11)
The present invention relates to methods for preparation of lycopenes, especially to lycopenes with high all-E contents or high 6Z contents from C15-Wittig salts mixtures (with high all-E-contents and high 6Z-contents, respectively). C15-Wittig salts mixtures are purified and 6Z-C15-Wittig salts are extracted from the mixtures. The extracted 6Z-C 15-Wittig salts are used in the synthesis of lycopenes with high 6Z contents and the residues are used in the synthesis of lycopenes with high all-E contents.
INTERMEDIATE OF LYCOPENE AND PREPARATION METHOD OF INTERMEDIATE
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Paragraph 0098; 0099; 0100; 0101; 0102; 0103; 0104, (2014/02/15)
The present invention relates to 2,6,10-trimethyl-3,5,9-undecatrienyl-1-aldehyde represented by formula (3), and a method for preparing this intermediate. The process route of the present invention is simple, the starting materials are available easily, and the cost is low.
