Lycopene

Base Information

• Chemical Name: Lycopene
• CAS No.: 502-65-8
• Deprecated CAS: 7634-65-3,25453-98-9,360790-67-6
• Molecular Formula: C40H56
• Molecular Weight: 536.885
• Hs Code.: 32030019
• European Community (EC) Number: 207-949-1
• UNII: SB0N2N0WV6
• DSSTox Substance ID: DTXSID2046593
• Nikkaji Number: J6.206E,J617.462K
• Wikipedia: Lycopene
• Wikidata: Q208130
• NCI Thesaurus Code: C2226
• RXCUI: 29008
• Metabolomics Workbench ID: 28982,200738
• ChEMBL ID: CHEMBL501174
• Mol file: 502-65-8.mol

Synonyms:All trans Lycopene;all-trans-lycopene;LYC O MATO;LYC-O-MATO;LYCOMATO;lycopene;lycopene, (13-cis)-isomer;Lycopene, (7-cis,7'-cis,9-cis,9'-cis)-isomer -;lycopene, (cis)-isomer;Pro Lycopene;Pro-Lycopene;prolycopene

Chemical Property of Lycopene

Chemical Property:

• Appearance/Colour: Pink Powder
• Vapor Pressure: 1.33E-16mmHg at 25°C
• Melting Point: 172-173 °C
• Refractive Index: 1.53
• Boiling Point: 660.9 °C at 760 mmHg
• Flash Point: 350.7 °C
• PSA: 0.00000
• Density: 0.888 g/cm³
• LogP: 12.93800
• Storage Temp.: −70°C
• Solubility.: Benzene (Slightly), Chloroform (Sparingly), Ethyl Acetate (Very Slightly), Metha
• XLogP3: 15.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 16
• Exact Mass: 536.438201786
• Heavy Atom Count: 40
• Complexity: 1050

Purity/Quality:

99%, ^*data from raw suppliers

Lycopene ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC(=CCCC(=CC=CC(=CC=CC(=CC=CC=C(C)C=CC=C(C)C=CC=C(C)CCC=C(C)C)C)C)C)C
• Isomeric SMILES: CC(=CCC/C(=C/C=C/C(=C/C=C/C(=C/C=C/C=C(/C=C/C=C(/C=C/C=C(/CCC=C(C)C)\C)\C)\C)/C)/C)/C)C
• Recent ClinicalTrials: The Effect of Lycopene on Sperm Quality in Men Attending Fertility Clinic
• Recent NIPH Clinical Trials: The effects of improvement of function of high density lipoprotein cholesterol, endothelial function, and suppressioun of oxidative stress by lycopene supplement after cardiac rehabilitation.
• Chemical Composition and Sources: Lycopene is a tetraterpene compound belonging to the carotenoid family. Abundantly found in tomatoes and tomato-based products. Also present in other fruits and vegetables, responsible for their yellow, orange, and red pigmentation.
• Health-Promoting Properties: While not considered an essential nutrient, lycopene is recommended for dietary intake due to its health-promoting properties. Acts as an antioxidant, protecting lipids, proteins, and DNA from oxidative damage.; Modulates cell growth and expression of certain blood levels and plays a role in immune and inflammatory processes.; Bioavailability is low, and circulating levels serve as prognostic data for health outcomes.
• Stability and Isomerization: Lycopene structure is sensitive to thermal treatment and oxidative processes. Vulnerable to light, oxygen, high temperature, acids, catalysts, and metal ions.; Undergoes isomerization to produce various mono- or poly-cis isomers.
• Absorption and Factors Influencing Absorption: Absorption is similar to dietary fat absorption. Influenced by age, gender, hormonal status, smoking, alcohol, and other dietary components.
• Role as an Antioxidant: Prevents autoxidation of fats and related products, contributing to its importance as an antioxidant.; Tomatoes, a major source of lycopene, exhibit antioxidant potential largely attributed to lycopene compounds.
• Production and Uses: Commercially available through chemical synthesis, fermentation, or isolation from natural sources like algae, fungi, and plants. Used in functional foods, cosmetics, and cosmeceutical products due to its biological properties.

Technology Process of Lycopene

There total 108 articles about Lycopene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 79.0%

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 (1116695-25-0) → lycopene (502-65-8)

Guidance literature:

With potassium methanolate; In cyclohexane; benzene; at 70 - 80 ℃; for 13h;

Reference yield: 79.0%

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 (1116695-25-0) → lycopene (502-65-8) + (9Z)-lycophene (64727-64-6)

Guidance literature:

With potassium methanolate; In cyclohexane; benzene; at 70 - 80 ℃; for 13h; Inert atmosphere;

DOI:10.1002/adsc.200700484

Reference yield: 78.0%

7,7',11,11'-tetra(phenylsulfonyl)-7,7',8,8',11,11',12,12'-octahydrolycopene (359643-76-8) → lycopene (502-65-8) + (9Z)-lycophene (64727-64-6)

Guidance literature:

With sodium ethanolate; In ethanol; Heating;

DOI:10.1002/1521-3773(20011001)40:19<3627::AID-ANIE3627>3.0.CO;2-E

upstream raw materials:

tetrachloromethane

N-Bromosuccinimide

all-trans-neurosporene

acetic acid

Downstream raw materials:

(+/-)-5,6-dihydro-ψ,ψ-carotene-5r_F,6t_F-diol

6-Methyl-hept-5-en-2-on

apo-6'-lycopenal

lycopene

Refernces

• 1、 Shen, Runpu,Jiang, Xiaoyue,Ye, Weidong,Song, Xiaohua,Liu, Luo,Lao, Xuejun,Wu, Chunlei. "A novel and practical synthetic route for the total synthesis of lycopene". . p. 5610 - 5614. Retrieved 2011.
• 2、 -. "Method for preparing lycopene". Paragraph 0047-0051; 0053-0056; 0058-0061. . Retrieved 2017/12/30.
• 3、 -. "Method for preparing lycopene". . . Retrieved 2017/05/03.