13190-97-1

Basic information

• Product Name: Solanesol
• Synonyms: (z,z,z,z,z,z,e,e)-amethyl;2,6,10,14,18,22,26,30,34-hexatriacontanonaen-1-ol,3,7,11,15,19,23,27,31,35-non;betulanonaprenol;betulaprenol9;nonaisoprenol;solanesolfromtobaccoleaves;3,7,11,15,19,23,27,31,35-NONAMETHYLHEXATRIACONTA-2,6,10,14,18,22,26,30,34-NONAEN-1-OL;SOLANESOL
• CAS NO: 13190-97-1
• Molecular Formula: C₄₅H₇₄O
• Molecular Weight: 631.07
• EINECS: 1308068-626-2
• Product Categories: Miscellaneous Natural Products;Nicotine Derivatives;Biochemistry;Terpenes;Terpenes (Others);Natural Plant Extract;Plant extract
• Mol File: 13190-97-1.mol

Chemical Properties

• Melting Point: 33°C
• Boiling Point: 685.6 °C at 760 mmHg
• Flash Point: 130.2 °C
• Appearance: brown waxy solid
• Density: 0.889 g/cm³
• Vapor Pressure: 9.21E-22mmHg at 25°C
• Refractive Index: 1.506
• Storage Temp.: −20°C
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• PKA: 14.42±0.10(Predicted)
• Stability: Stable, but may be heat sensitive - store cold. Combustible. Incompatible with strong oxidizing agents.
• Merck: 14,8703
• CAS DataBase Reference: Solanesol(CAS DataBase Reference)
• NIST Chemistry Reference: Solanesol(13190-97-1)
• EPA Substance Registry System: Solanesol(13190-97-1)

Safety Data

• Safety Statements: 24/25
• WGK Germany: 3
• RTECS: MP5366666
• Hazardous Substances Data: 13190-97-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Solanesol is used as an important pharmaceutical intermediate due to its anti-ulcer and anti-tumor properties. It plays a crucial role in the development of medications for various health conditions.
Used in Synthesis of Coenzyme Q10:
Solanesol is used as an important raw material for the synthesis of coenzyme Q10. Coenzyme Q10 serves as an activator of human cell respiration and metabolism and acts as an immune enhancer for the body.
Used in Synthesis of Vitamin K2:
Solanesol can also be used as an intermediate in the synthesis of vitamin K2, which is essential for various bodily functions.
Used in Antioxidant and Antibacterial Applications:
Solanesol exhibits antioxidant and antibacterial properties, making it useful in various applications, such as in the development of products for the healthcare and personal care industries.
Used in Environmental Exposure Studies:
Solanesol can be used as a tracer for environmental exposure to tobacco smoke, helping to understand the impact of tobacco use on the environment and human health.
Used in Tobacco Industry:
Solanesol is an important precursor of the tumorigenicity polynuclear aromatic hydrocarbons in tobacco leaves, making it a significant component in the tobacco industry.

Market investigation

Solanesol is a kind of natural product that is widely presented higher plants, mammals, and microorganisms. It is a waxy white solid with the melting point being 33~42.5 ℃. It is insoluble in water and soluble in various kinds of organic solvents. Its natural product belongs to all-trans isomer. It was first isolated in 1956 by the R.L. Rowland et al from plants. In 1959, Frickson et al have adopted nuclear magnetic resonance spectroscopy to demonstrate that solanesol is a kind of tri-sesquiterpene alcohol consisting of nine isoprene units. And later, it was discovered that the tobacco has a relative high solanesol content within the range of about 0.3 to 0.5%. It has also been reported that the solanesol content in Yunnan tobacco leaves is within the range of 0.5-0.8%. Now people generally applied discarded tobacco as raw material, first extract the crude product of solanesol (containing 17% solanesol), after a certain process of extracting refined solanesol product (content 70-75%) and then pure product (content 90%), and then mainly used for synthesis of coenzyme Q10 (CoenzymeQl0) and vitamin K2. China is a big country of tobacco with the annual tobacco production output being over 5000kt, and therefore it is a great material resource in China. With the continued development of the tobacco industry, how to take better advantage of tobacco resources and improve its economic value are the subject and the challenges we face. Tobacco contains various kinds of natural chemicals including a variety of materials being able to be recycled such as nicotine, lipids, essential oils, proteins, amino acids, cellulose and so on. Among them, many are important biochemical pharmaceutical raw materials. As early as 1960 s in foreign countries, people have begun the comprehensive development and utilization of tobacco. It was not until the 1990 s when China had gradually begun to apply tobacco for the extraction of solanesol. Therefore, extracting the solanesol from tobacco (especially from waste tobacco) can not only to obtain an important kind of pharmaceutical raw materials but also turning waste into wealth and further increasing the added value of the tobacco industry.

The international market of the high-purity solanesol

in recent years, the growth of the international market demand of high-purity solanesol has reached as high as 15% to 20%. In 2004, the solanesol sales of the international market is 4,000 tons while this value had increased to 5200 tons in 2006 and increased to 7500 tons in 2008. It has also been predicted that the international market demand for the high-purity solanesol will reach to the value of 8000 to 10,000 tons. The hot selling of solanesol should thank to the rapid popularization of its downstream products Coenzyme Q10 (CoQ10) in the international market. China is the largest producer of tobacco and has a great wealth of the raw material of extracting the solanesol. With the rapid improvement of the solanesol extraction process year by year, there have been several production lines of high-purity solanesol in places such as Jilin and Jiangsu that are under construction or subjecting to trial production. High-purity solanesol is the main intermediate for synthesizing of CoQ10, vitamin K2 and other best-selling drug. Researchers of western medicine have found that high-purity solanesol itself can be directly used as a clinical drug for application with the clinical application of anti-heart failure, liver treatment damage and adjuvant treatment of cancer. According to the report of the "Indian Medicine", currently there are many hospitals in India that are processing the clinical controlled drugs of "preparation of high purity solanesol as diabetes therapeutic agents and anti-cancer drugs". If once the novel application above has gotten recognition from the medical community, it is sure that people will greatly promote the total sales amount of the high-purity solanesol in the international market in the future. In addition, the application of solanesol in synthesis of CoQ10 has draw great attention from the pharmaceutical industry in Europe with the related findings being continuously emerged in many publication processes such as: it is able to promote the oxidative phosphorylation and adenosine triphosphate (ATP) synthesis; it can be used as the activator of cell metabolism and respiration; it can help enhance the body's immune system and so on. So far, CoQ10 has been listed into the pharmacopoeia of United States, Europe, Japan and other countries. In recent years, the US pharmaceutical researchers have also found that the combination of CoQ10 with statin cholesterol-lowering drugs can greatly reduce side effects of the later drugs in causing rhabdomyolysis and prevention the acute myocardial infarction of patients of coronary heart disease. It is worth mentioning that, in a current time with drug safety accidents frequently happening, it has yet to see reports regarding the side effects of CoQ10. In recent years, CoQ10 has got rapid increase in the growth rate of its market sales in the United States, Australia, and European countries such as Germany, Italy and France, Japan and China. According to the latest statistics from abroad last year, the total global CoQ10 drug sales have exceeded more than 1000 tons with its scope covering drugs, cosmetics and health food products. Therefore, CoQ10 is considered one of medicine with the greatest potential for growth in the 21st century. From this perspective, no matter whether being used for synthesis of CoQ10 or being used as drug itself, with the deepening of research and practical applications, high purity solanesol will always reach its “golden period” of the market career. The above information is edited by the lookchem of Dai Xiongfeng.

Output analysis

According to statistics, in 2008, the status of the CoQ10 global output in the world's major drug production countries were: Japan, 600 tons; the United States, 200 tons; South Korea, 200 tons; Germany, Italy 100 tons in total; China about 30 tons. According to this estimation, the global actual output amount of CoQ10 in last year is about 1,200 tons. If calculated according to “the production of 1 ton per CoQ10 consumes two tons of raw material of high purity solanesol”, the amount of the high-purity solanesol only used for the synthesis of CoQ10 has reached about 2400 tons, plus the consumption amount of high-purity solanesol in other kinds of applications such as cosmetics, health foods and so on, it is estimated that the total global output of high-purity solanesol in last year should be around 6,000 tons. Since the crude solanesol extracted from tobacco leaves only has the highest content of being 20% which is insufficient for being as the raw material for the synthesis of CoQ10 and other kinds of drugs, only when its purity increased to 90% can it be used as the raw material for synthesizing the drug. At present, the price of the high-purity solanesol in the international market is generally around $ 300 per kg while the average exported price of China's high purity solanesol is about $ 250 per kilogram. But at a few years ago, China can only synthesize the crude solanesol product and also need to import more than 1,000 tons per year of high-purity solanesol from Japan as domestic raw materials for the synthesis of CoQ10 and other drugs. The most common process for the production of CoQ10 includes synthesis method (the major raw material is high purity solanesol) and microbial fermentation. Japan is one of the several few countries in the world that being able to perform these two kinds of CoQ10 production process, and is also world's leading exporter of CoQ10. According to statistics, the number of exported CoQ10 in Japan has ever accounted for about 90% of the total sales of CoQ10 in the international market. However, for the main raw material for the synthesis of CoQ10-the high purity solanesol, Japan has ever adopted self-production. However, with the increasing capability of China, India in producing the crude solanesol, Japan has instead shifted to import crude solanesol from China and India and then further increase the purity in order to apply for the synthesis CoQ10 before being re-exported to European markets. Data have shown that previously the annual exported amount of solanesol to Japan accounts for about 60% of China's total exported amount of crude solanesol. It is understood that although the tobacco production of India is less than that of China, however, it has an earlier development of industrial solanesol extraction than China. Its solanesol product also has fierce competition with China in the international market.

InChI:InChI=1/C45H74O/c1-37(2)19-11-20-38(3)21-12-22-39(4)23-13-24-40(5)25-14-26-41(6)27-15-28-42(7)29-16-30-43(8)31-17-32-44(9)33-18-34-45(10)35-36-46/h19,21,23,25,27,29,31,33,35,46H,11-18,20,22,24,26,28,30,32,34,36H2,1-10H3/b38-21+,39-23+,40-25+,41-27+,42-29+,43-31+,44-33+,45-35+

Synthetic route

(2E,6E,10E,14E,18E,22E,26E,30E)-3,7,11,15,19,23,27,31,35-nonamethyl-5-p-tolylsulphonylhexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-ol → solanesol (13190-97-1)

Conditions	Yield
With lithium; ethylamine In diethyl ether at -78℃;	50%

(2E,6E)-3,7,11-trimethyl-1-(p-tolylsulfonyl)dodeca-2,6,10-triene (68690-45-9, 80370-68-9, 53254-63-0) + (2E,6E,10E)-1-Benzyloxy-3,7,11-trimethyldodeca-2,6,10-trien-12-ol (71135-48-3) + (2E,6E,10E)-2,6,10-trimethyl-12-(toluene-4-sulfonyl)-dodeca-2,6,10-trien-1-ol (70238-40-3) → solanesol (13190-97-1)

Conditions	Yield
Multistep reaction;

3,7-dimethyl-2E,6-octadien-1-yl acetate (105-87-3) → solanesol (13190-97-1)

Conditions	Yield
Multi-step reaction with 14 steps 1: 44 percent / SeO2 / aq. ethanol / 9 h / Heating 2: 72 percent / NaBH4 / methanol / 5 h / -10 °C 3: 94 percent / PBr3, pyridine / diethyl ether / 6 h / 0 °C 4: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h 5: 5percent sodium amalgam, disodium hydrogen phosphate / methanol / 2 h / 0 °C 6: 91 percent / PBr3, pyridine / diethyl ether / 6 h / -5 °C 7: 78 percent / dimethylformamide / 24 h / Ambient temperature 8: 1.) n-BuLi, 3.) H2O, KOH 9: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 10: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 11: 1.) n-BuLi, 3.) H2O, KOH 12: 70 percent / Li, ethylamine / diethyl ether 13: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 14: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme
Multi-step reaction with 13 steps 1: 44 percent / SeO2 / aq. ethanol / 9 h / Heating 2: 72 percent / NaBH4 / methanol / 5 h / -10 °C 3: 94 percent / PBr3, pyridine / diethyl ether / 6 h / 0 °C 4: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h 5: NaOMe / methanol / 2 h / Ambient temperature 7: 1.) n-BuLi, 3.) H2O, KOH 8: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 9: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 10: 1.) n-BuLi, 3.) H2O, KOH 11: 70 percent / Li, ethylamine / diethyl ether 12: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 13: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme
Multi-step reaction with 15 steps 1: 44 percent / SeO2 / aq. ethanol / 9 h / Heating 2: 72 percent / NaBH4 / methanol / 5 h / -10 °C 3: 94 percent / PBr3, pyridine / diethyl ether / 6 h / 0 °C 4: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h 5: NaOMe / methanol / 2 h / Ambient temperature 6: 264 mg / Li, ethylamine / diethyl ether / 1 h / -78 °C 7: 91 percent / PBr3, pyridine / diethyl ether / 6 h / -5 °C 8: 78 percent / dimethylformamide / 24 h / Ambient temperature 9: 1.) n-BuLi, 3.) H2O, KOH 10: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 11: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 12: 1.) n-BuLi, 3.) H2O, KOH 13: 70 percent / Li, ethylamine / diethyl ether 14: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 15: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme

2E,6E,10E-geranylgeranyl bromide (50848-64-1) → solanesol (13190-97-1)

Conditions

Yield

Multi-step reaction with 8 steps 1: 78 percent / dimethylformamide / 24 h / Ambient temperature 2: 1.) n-BuLi, 3.) H2O, KOH 3: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 4: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 5: 1.) n-BuLi, 3.) H2O, KOH 6: 70 percent / Li, ethylamine / diethyl ether 7: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 8: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme

(2E,6E)-8-bromo-3,7-dimethylocta-2,6-dienyl acetate (37905-04-7) → solanesol (13190-97-1)

Conditions	Yield
Multi-step reaction with 11 steps 1: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h 2: 5percent sodium amalgam, disodium hydrogen phosphate / methanol / 2 h / 0 °C 3: 91 percent / PBr3, pyridine / diethyl ether / 6 h / -5 °C 4: 78 percent / dimethylformamide / 24 h / Ambient temperature 5: 1.) n-BuLi, 3.) H2O, KOH 6: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 7: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 8: 1.) n-BuLi, 3.) H2O, KOH 9: 70 percent / Li, ethylamine / diethyl ether 10: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 11: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme
Multi-step reaction with 10 steps 1: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h 2: NaOMe / methanol / 2 h / Ambient temperature 4: 1.) n-BuLi, 3.) H2O, KOH 5: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 6: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 7: 1.) n-BuLi, 3.) H2O, KOH 8: 70 percent / Li, ethylamine / diethyl ether 9: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 10: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme
Multi-step reaction with 12 steps 1: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h 2: NaOMe / methanol / 2 h / Ambient temperature 3: 264 mg / Li, ethylamine / diethyl ether / 1 h / -78 °C 4: 91 percent / PBr3, pyridine / diethyl ether / 6 h / -5 °C 5: 78 percent / dimethylformamide / 24 h / Ambient temperature 6: 1.) n-BuLi, 3.) H2O, KOH 7: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 8: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 9: 1.) n-BuLi, 3.) H2O, KOH 10: 70 percent / Li, ethylamine / diethyl ether 11: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 12: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme
Multi-step reaction with 7 steps 1: 1.) n-BuLi, 3.) H2O, KOH 2: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 3: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 4: 1.) n-BuLi, 3.) H2O, KOH 5: 70 percent / Li, ethylamine / diethyl ether 6: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 7: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme
Multi-step reaction with 4 steps 1: 1.) n-BuLi, 3.) H2O, KOH 2: 70 percent / Li, ethylamine / diethyl ether 3: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 4: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme

8-hydroxygeranyl acetate (37905-03-6) → solanesol (13190-97-1)

Conditions	Yield
Multi-step reaction with 12 steps 1: 94 percent / PBr3, pyridine / diethyl ether / 6 h / 0 °C 2: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h 3: 5percent sodium amalgam, disodium hydrogen phosphate / methanol / 2 h / 0 °C 4: 91 percent / PBr3, pyridine / diethyl ether / 6 h / -5 °C 5: 78 percent / dimethylformamide / 24 h / Ambient temperature 6: 1.) n-BuLi, 3.) H2O, KOH 7: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 8: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 9: 1.) n-BuLi, 3.) H2O, KOH 10: 70 percent / Li, ethylamine / diethyl ether 11: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 12: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme
Multi-step reaction with 11 steps 1: 94 percent / PBr3, pyridine / diethyl ether / 6 h / 0 °C 2: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h 3: NaOMe / methanol / 2 h / Ambient temperature 5: 1.) n-BuLi, 3.) H2O, KOH 6: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 7: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 8: 1.) n-BuLi, 3.) H2O, KOH 9: 70 percent / Li, ethylamine / diethyl ether 10: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 11: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme
Multi-step reaction with 13 steps 1: 94 percent / PBr3, pyridine / diethyl ether / 6 h / 0 °C 2: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h 3: NaOMe / methanol / 2 h / Ambient temperature 4: 264 mg / Li, ethylamine / diethyl ether / 1 h / -78 °C 5: 91 percent / PBr3, pyridine / diethyl ether / 6 h / -5 °C 6: 78 percent / dimethylformamide / 24 h / Ambient temperature 7: 1.) n-BuLi, 3.) H2O, KOH 8: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 9: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 10: 1.) n-BuLi, 3.) H2O, KOH 11: 70 percent / Li, ethylamine / diethyl ether 12: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 13: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme
Multi-step reaction with 8 steps 1: 94 percent / PBr3, pyridine / diethyl ether / 6 h / 0 °C 2: 1.) n-BuLi, 3.) H2O, KOH 3: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 4: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 5: 1.) n-BuLi, 3.) H2O, KOH 6: 70 percent / Li, ethylamine / diethyl ether 7: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 8: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme
Multi-step reaction with 5 steps 1: 94 percent / PBr3, pyridine / diethyl ether / 6 h / 0 °C 2: 1.) n-BuLi, 3.) H2O, KOH 3: 70 percent / Li, ethylamine / diethyl ether 4: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 5: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme

(2E,6E)-3,7-dimethyl-8-oxoocta-2,6-dien-1-yl acetate (37905-02-5) → solanesol (13190-97-1)

Conditions	Yield
Multi-step reaction with 13 steps 1: 72 percent / NaBH4 / methanol / 5 h / -10 °C 2: 94 percent / PBr3, pyridine / diethyl ether / 6 h / 0 °C 3: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h 4: 5percent sodium amalgam, disodium hydrogen phosphate / methanol / 2 h / 0 °C 5: 91 percent / PBr3, pyridine / diethyl ether / 6 h / -5 °C 6: 78 percent / dimethylformamide / 24 h / Ambient temperature 7: 1.) n-BuLi, 3.) H2O, KOH 8: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 9: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 10: 1.) n-BuLi, 3.) H2O, KOH 11: 70 percent / Li, ethylamine / diethyl ether 12: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 13: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme
Multi-step reaction with 12 steps 1: 72 percent / NaBH4 / methanol / 5 h / -10 °C 2: 94 percent / PBr3, pyridine / diethyl ether / 6 h / 0 °C 3: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h 4: NaOMe / methanol / 2 h / Ambient temperature 6: 1.) n-BuLi, 3.) H2O, KOH 7: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 8: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 9: 1.) n-BuLi, 3.) H2O, KOH 10: 70 percent / Li, ethylamine / diethyl ether 11: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 12: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme
Multi-step reaction with 14 steps 1: 72 percent / NaBH4 / methanol / 5 h / -10 °C 2: 94 percent / PBr3, pyridine / diethyl ether / 6 h / 0 °C 3: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h 4: NaOMe / methanol / 2 h / Ambient temperature 5: 264 mg / Li, ethylamine / diethyl ether / 1 h / -78 °C 6: 91 percent / PBr3, pyridine / diethyl ether / 6 h / -5 °C 7: 78 percent / dimethylformamide / 24 h / Ambient temperature 8: 1.) n-BuLi, 3.) H2O, KOH 9: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 10: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 11: 1.) n-BuLi, 3.) H2O, KOH 12: 70 percent / Li, ethylamine / diethyl ether 13: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 14: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme

Geranylgeraniol (24034-73-9) → solanesol (13190-97-1)

Conditions

Yield

Multi-step reaction with 9 steps 1: 91 percent / PBr3, pyridine / diethyl ether / 6 h / -5 °C 2: 78 percent / dimethylformamide / 24 h / Ambient temperature 3: 1.) n-BuLi, 3.) H2O, KOH 4: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 5: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 6: 1.) n-BuLi, 3.) H2O, KOH 7: 70 percent / Li, ethylamine / diethyl ether 8: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 9: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme

3,7-dimethyl-1-(p-toluenesulfonyl)-2(E),6-octadiene (53254-60-7) → solanesol (13190-97-1)

Conditions	Yield
Multi-step reaction with 11 steps 1: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h 2: 5percent sodium amalgam, disodium hydrogen phosphate / methanol / 2 h / 0 °C 3: 91 percent / PBr3, pyridine / diethyl ether / 6 h / -5 °C 4: 78 percent / dimethylformamide / 24 h / Ambient temperature 5: 1.) n-BuLi, 3.) H2O, KOH 6: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 7: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 8: 1.) n-BuLi, 3.) H2O, KOH 9: 70 percent / Li, ethylamine / diethyl ether 10: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 11: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme
Multi-step reaction with 10 steps 1: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h 2: NaOMe / methanol / 2 h / Ambient temperature 4: 1.) n-BuLi, 3.) H2O, KOH 5: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 6: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 7: 1.) n-BuLi, 3.) H2O, KOH 8: 70 percent / Li, ethylamine / diethyl ether 9: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 10: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme
Multi-step reaction with 12 steps 1: 1.) n-BuLi / 1.) THF, HMPA, hexane, -78 deg C, 1.5 h, 2.) 6 h 2: NaOMe / methanol / 2 h / Ambient temperature 3: 264 mg / Li, ethylamine / diethyl ether / 1 h / -78 °C 4: 91 percent / PBr3, pyridine / diethyl ether / 6 h / -5 °C 5: 78 percent / dimethylformamide / 24 h / Ambient temperature 6: 1.) n-BuLi, 3.) H2O, KOH 7: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 8: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 9: 1.) n-BuLi, 3.) H2O, KOH 10: 70 percent / Li, ethylamine / diethyl ether 11: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 12: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme

(E)-1-O-acetyl-4-chloro-3-methyl-2-buten-1-ol (24529-80-4) → solanesol (13190-97-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 2: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme

(E,E,E,E,E,E,E)-3,7,11,15,19,23,27,31-octamethyldotriaconta-2,6,10,14,18,22,26,30-octaen-1-ol (33569-79-8) → solanesol (13190-97-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 2: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme

(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyltetracosa-2,6,10,14,18,22-hexaen-1-ol (68778-93-8) → solanesol (13190-97-1)

Conditions	Yield
Multi-step reaction with 5 steps 1: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 2: 1.) n-BuLi, 3.) H2O, KOH 3: 70 percent / Li, ethylamine / diethyl ether 4: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 5: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme

1-methyl-4-{[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]sulfonyl}benzene (68690-47-1) → solanesol (13190-97-1)

Conditions	Yield
Multi-step reaction with 7 steps 1: 1.) n-BuLi, 3.) H2O, KOH 2: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 3: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 4: 1.) n-BuLi, 3.) H2O, KOH 5: 70 percent / Li, ethylamine / diethyl ether 6: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 7: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme

(2E,6E,10E)-3,7,11,15-tetramethyl-9-p-tolylsulphonylhexadeca-2,6,10,14-tetraen-1-ol (71816-56-3) → solanesol (13190-97-1)

Conditions	Yield
Multi-step reaction with 8 steps 2: 1.) n-BuLi, 3.) H2O, KOH 3: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 4: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 5: 1.) n-BuLi, 3.) H2O, KOH 6: 70 percent / Li, ethylamine / diethyl ether 7: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 8: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme
Multi-step reaction with 10 steps 1: 264 mg / Li, ethylamine / diethyl ether / 1 h / -78 °C 2: 91 percent / PBr3, pyridine / diethyl ether / 6 h / -5 °C 3: 78 percent / dimethylformamide / 24 h / Ambient temperature 4: 1.) n-BuLi, 3.) H2O, KOH 5: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 6: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 7: 1.) n-BuLi, 3.) H2O, KOH 8: 70 percent / Li, ethylamine / diethyl ether 9: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 10: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme

(2E,6E,10E)-3,7,11,15-tetramethyl-9-[(4-methylphenyl)sulfonyl]hexadeca-2,6,10,14-tetraen-1-yl acetate (73127-51-2) → solanesol (13190-97-1)

Conditions	Yield
Multi-step reaction with 10 steps 1: 5percent sodium amalgam, disodium hydrogen phosphate / methanol / 2 h / 0 °C 2: 91 percent / PBr3, pyridine / diethyl ether / 6 h / -5 °C 3: 78 percent / dimethylformamide / 24 h / Ambient temperature 4: 1.) n-BuLi, 3.) H2O, KOH 5: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 6: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 7: 1.) n-BuLi, 3.) H2O, KOH 8: 70 percent / Li, ethylamine / diethyl ether 9: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 10: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme
Multi-step reaction with 9 steps 1: NaOMe / methanol / 2 h / Ambient temperature 3: 1.) n-BuLi, 3.) H2O, KOH 4: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 5: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 6: 1.) n-BuLi, 3.) H2O, KOH 7: 70 percent / Li, ethylamine / diethyl ether 8: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 9: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme
Multi-step reaction with 11 steps 1: NaOMe / methanol / 2 h / Ambient temperature 2: 264 mg / Li, ethylamine / diethyl ether / 1 h / -78 °C 3: 91 percent / PBr3, pyridine / diethyl ether / 6 h / -5 °C 4: 78 percent / dimethylformamide / 24 h / Ambient temperature 5: 1.) n-BuLi, 3.) H2O, KOH 6: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 7: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 8: 1.) n-BuLi, 3.) H2O, KOH 9: 70 percent / Li, ethylamine / diethyl ether 10: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 11: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme

(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyl-1-p-tolylsulphonyltetracosa-2,6,10,14,18,22-hexaene (68690-49-3) → solanesol (13190-97-1)

Conditions	Yield
Multi-step reaction with 4 steps 1: 1.) n-BuLi, 3.) H2O, KOH 2: 70 percent / Li, ethylamine / diethyl ether 3: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 4: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme

(2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyl-9-p-tolylsulphonyltetracosa-2,6,10,14,18,22-hexaen-1-ol (78284-77-2) → solanesol (13190-97-1)

Conditions	Yield
Multi-step reaction with 6 steps 1: 63 percent / Li, ethylamine / diethyl ether / 1 h / -78 °C 2: 1.) PBr3, pyridine / 1.) ether, 2.) DMF, ambient temperature 3: 1.) n-BuLi, 3.) H2O, KOH 4: 70 percent / Li, ethylamine / diethyl ether 5: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 6: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme

(2E,6E,10E,14E,18E,22E,26E)-3,7,11,15,19,23,27,31-octamethyl-9-p-tolylsulphonyldotriaconta-2,6,10,14,18,22,26,30-octaen-1-ol → solanesol (13190-97-1)

Conditions	Yield
Multi-step reaction with 3 steps 1: 70 percent / Li, ethylamine / diethyl ether 2: 1.) n-BuLi / 1.) THF, HMPA, 2.) -78 deg C 3: 50 percent / Li, ethylamine / diethyl ether / -78 °C View Scheme

solanesol (13190-97-1) → solanesyl bromide (52610-77-2)

Conditions	Yield
With pyridine; phosphorus tribromide In diethyl ether	99%
With phosphorus tribromide; triethylamine In di-isopropyl ether at -10℃; for 2h; Product distribution / selectivity;	94%
With phosphorus tribromide In tetrahydrofuran at -10℃; for 2h; Product distribution / selectivity;	88%

solanesol (13190-97-1) → solanesyl chloride (138647-72-0)

Conditions	Yield
With phosphorus trichloride In N,N-dimethyl-formamide at 20℃; for 1h;	96.1%
With N,N-dimethyl-formamide; phosphorus trichloride In tetrahydrofuran at 20℃; for 2h;	95.1%
With N,N-dimethyl-formamide; phosphorus trichloride In tetrahydrofuran at 20℃; for 2h; Product distribution / selectivity;	95.1%

solanesol (13190-97-1) + phosphoric acid mono-[3,4-bis-(tert-butyl-dimethyl-silanyloxy)-5-(tert-butyl-dimethyl-silanyloxymethyl)-tetrahydro-furan-2-yl] ester → C68H125O8PSi3 (1353003-10-7)

Conditions	Yield
With pyridine; trichloroacetonitrile at 80℃; for 1h; Microwave irradiation;	84%

solanesol (13190-97-1) + C14H21O13P (270076-37-4) → C59H93O13P (1353002-97-7)

Conditions	Yield
With pyridine; trichloroacetonitrile at 80℃; for 1h; Microwave irradiation;	82%

solanesol (13190-97-1) + chloroacetyl chloride (79-04-9) → chloro-acetic acid 3,7,11,15,19,23,27,31,35-nonamethyl-hexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-yl ester (1190409-13-2)

Conditions	Yield
With triethylamine In benzene at 5℃; for 4h;	80.3%

succinic acid anhydride (108-30-5) + solanesol (13190-97-1) → succinic acid mono-(3,7,11,15,19,23,27,31,35-nonamethyl-hexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-yl) ester (630393-89-4)

Conditions	Yield
With pyridine; dmap at 20℃; for 6h;	80%
With dmap; triethylamine In dichloromethane at 20℃; for 48h;	70%
With pyridine; dmap at 20℃; for 6h;
With dmap; triethylamine In dichloromethane; N,N-dimethyl-formamide at 20℃; for 48h; Inert atmosphere;

solanesol (13190-97-1) + 3-methoxycinnamic acid (6099-04-3) → 3-(3-methoxy-phenyl)-acrylic acid 3,7,11,15,19,23,27,31,35-nonamethyl-hexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-yl ester

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 6h;	80%

solanesol (13190-97-1) + phenylpropyolic acid (637-44-5) → (2E,6E,10E,14E,18E,22E,26E,30E)-3,7,11,15,19,23,27,31,35-nonamethylhexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-yl 3-phenylpropiolate

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 25℃; for 6h;	69%

solanesol (13190-97-1) + 3-Methylbutenoic acid (541-47-9) → 3-methyl-but-2-enoic acid 3,7,11,15,19,23,27,31,35-nonamethyl-hexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-yl ester (1190409-09-6)

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 6h;	66.3%

solanesol (13190-97-1) + 3-(4'-methoxyphenyl)propenoic acid (830-09-1) → 3-(4-methoxy-phenyl)-acrylic acid 3,7,11,15,19,23,27,31,35-nonamethyl-hexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-yl ester

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 6h;	64%

solanesol (13190-97-1) + 2,3-dimethoxy-5-methylbenzene-1,4-diol (3066-90-8) → ubiquinone-45 (303-97-9)

Conditions	Yield
Stage #1: solanesol; 2,3-dimethoxy-5-methylbenzene-1,4-diol With phosphotungstic acid In nitromethane; n-heptane; water at 40℃; for 3h; Stage #2: With acetic acid; silver(l) oxide In n-heptane at 20℃; for 1h; Product distribution / selectivity;	63%
With acetic acid; zinc(II) chloride Behandeln des Reaktionsprodukts mit Ag2O in Aether;

solanesol (13190-97-1) + 2,3,4,5-tetramethoxytoluene (35896-58-3) → 1,2,3,4-tetramethoxy-5-methyl-6-((2E,6E,10E,14E,18E,22E,26E,30E)-3,7,11,15,19,23,27,31,35-nonamethyl-hexatriaconta-2,6,10,14,18,22,26,30,34-nonaenyl)-benzene

Conditions	Yield
With bismuth(lll) trifluoromethanesulfonate In nitromethane; hexane at 50℃; for 12h; Product distribution / selectivity;	62.9%
With scandium tris(trifluoromethanesulfonate) In nitromethane; hexane at 50℃; for 16h; Product distribution / selectivity;	32%
With bismuth(lll) trifluoromethanesulfonate In nitromethane; n-heptane at 50℃; for 12h; Product distribution / selectivity;

solanesol (13190-97-1) + 3-(2'-methoxyphenyl)propenoic acid (6099-03-2) → 3-(2-methoxy-phenyl)-acrylic acid 3,7,11,15,19,23,27,31,35-nonamethyl-hexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-yl ester

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 6h;	61%

solanesol (13190-97-1) + C26H34O15 → 6-acetoxy-1-(3,4,5,6-tetraacetoxy-tetrahydro-pyran-2-yloxy)-7-methyl-1,4a,5,6,7,7a-hexahydro-cyclopenta[c]pyran-4-carboxylic acid 3,7,11,15,19,23,27,31,35-nonamethyl-hexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-yl ester

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 6h;	60%

3,4,5-trimethoxycinnamic acid (90-50-6) + solanesol (13190-97-1) → 3-(3,4,5-trimethoxy-phenyl)-acrylic acid 3,7,11,15,19,23,27,31,35-nonamethyl-hexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-yl ester

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 6h;	60%

solanesol (13190-97-1) + 2,3,4-trimethoxy-6-methylphenol (39068-88-7) → 2,3,4-trimethoxy-6-methyl-5-solanesylphenol (110582-10-0)

Conditions	Yield
With scandium tris(trifluoromethanesulfonate) In nitromethane; hexane at 50℃; for 16h; Product distribution / selectivity;	51%
With bismuth(lll) trifluoromethanesulfonate In nitromethane; n-heptane at 50℃; for 12h; Product distribution / selectivity;

solanesol (13190-97-1) + 3-(2-furyl)acrylic acid (539-47-9) → 3-furan-2-yl-acrylic acid 3,7,11,15,19,23,27,31,35-nonamethyl-hexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-yl ester

Conditions	Yield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 6h;	50%

solanesol (13190-97-1) + methyl chloroformate (79-22-1) → solanesyl methyl carbonate

Conditions	Yield
Stage #1: solanesol With pyridine; dmap In dichloromethane at 5℃; for 0.166667h; Sealed tube; Inert atmosphere; Stage #2: methyl chloroformate In dichloromethane at 5 - 20℃; for 1.16667h; Sealed tube; Inert atmosphere;	46%

solanesol (13190-97-1) + 2,3-dimethoxy-5-methylbenzene-1,4-diol (3066-90-8) → ubiquinone-45 (303-97-9) + ubiquinone-9 (5677-54-3)

Conditions	Yield
With scandium tris(trifluoromethanesulfonate) In nitromethane; hexane at 50℃; for 16h;	A 11.6% B 40.4%

solanesol (13190-97-1) + tetrabutylammonium dihydrogen phosphate → tetrabutylammonium solanesyl phosphate

Conditions	Yield
Stage #1: solanesol; tetrabutylammonium dihydrogen phosphate With trichloroacetonitrile In dichloromethane at 20℃; for 1h; Inert atmosphere; Darkness; Stage #2: With ammonium hydroxide In tetrahydrofuran; water at 20℃; for 14h; Inert atmosphere;	33%

ammonium hydroxide (1336-21-6) + solanesol (13190-97-1) → C45H76O7P2*3H3N

Conditions	Yield
Stage #1: solanesol With tetrabutylammonium dihydrogen phosphate; trichloroacetonitrile In dichloromethane at 20℃; for 14h; Darkness; Stage #2: ammonium hydroxide In tetrahydrofuran; dichloromethane at 20℃; for 0.5h;	32%

solanesol (13190-97-1) + tetrabutylammonium dihydrogen phosphate → C45H74O7P2(2-)*2C16H36N(1+)

Conditions	Yield
Stage #1: solanesol; tetrabutylammonium dihydrogen phosphate With trichloroacetonitrile In dichloromethane at 20℃; for 14h; Inert atmosphere; Darkness; Stage #2: With ammonium hydroxide In tetrahydrofuran; methanol; water; toluene at 20℃; for 1h; Inert atmosphere;	27%

solanesol (13190-97-1) + 3,4,5-triiodobenzoyl chloride (22205-68-1) → 3,4,5-triiodo-benzoic acid-(3,7,11,15,19,23,27,31,35-nonamethyl-hexatriaconta-2t,6t,10t,14t,18t,22t,26t,30t,34-nonaenyl ester) (124159-62-2)

solanesol (13190-97-1) → solanesylaldehyd (28973-76-4, 55528-85-3)

Conditions	Yield
With manganese(IV) oxide

solanesol (13190-97-1) → decaprenol (15575-04-9)

Conditions	Yield
ueber mehrere Zwischenstufen;
Multi-step reaction with 5 steps 1: PBr3 / pyridine / diethyl ether; petroleum ether / 2 h / 0 °C 2: Na / ethanol / 1,) 0 deg C, 3 h, 2.) 60 deg C, 4 h, 3.) r.t., overnight 3: 10percent aq. NaOH / ethanol / 1.) r.t., 2 h, 2.) 60 deg C, 3 h 4: 89 percent / NaH / tetrahydrofuran / 5 h / Heating 5: i-Bu2AlH / petroleum ether; cyclopentane / 3 h / Heating View Scheme
Multi-step reaction with 3 steps 1: 1.1 g / PBr3 / tetrahydrofuran / 0.42 h / -20 °C 2: 70 percent / 1.) n-BuLi / tetrahydrofuran; hexane / 1.) -70 deg C, 40 min, 2.) 40 min 3: Na / ethanol; tetrahydrofuran / 0.25 h / -40 °C View Scheme

solanesol (13190-97-1) → 2,6,10,14,18,22,26,30,34-nonamethyl-hexatriacontane (77621-63-7)

Conditions	Yield
With palladium on activated charcoal; ethanol Hydrogenation;

solanesol (13190-97-1) → 3,7,11,15,19,23,27,31,35-nonamethyl-hexatriacontan-1-ol (70495-48-6)

Conditions	Yield
With palladium on activated charcoal Hydrogenation;

solanesol (13190-97-1) → 3,5-dinitro-benzoic acid-(3,7,11,15,19,23,27,31,35-nonamethyl-hexatriaconta-2t,6t,10t,14t,18t,22t,26t,30t,34-nonaenyl ester) (108193-67-5)

solanesol (13190-97-1) + 3-nitrophthalic acid anhydride (641-70-3) → 3-nitro-phthalic acid-2-(3,7,11,15,19,23,27,31,35-nonamethyl-hexatriaconta-2t,6t,10t,14t,18t,22t,26t,30t,34-nonaenyl ester)

Upstream product

• 68690-45-9 (2E,6E)-3,7,11-trimethyl-1-(p-tolylsulfonyl)dodeca-2,6,10-triene 
• 71135-48-3 (2E,6E,10E)-1-Benzyloxy-3,7,11-trimethyldodeca-2,6,10-trien-12-ol 
• 70238-40-3 (2E,6E,10E)-2,6,10-trimethyl-12-(toluene-4-sulfonyl)-dodeca-2,6,10-trien-1-ol 
• 105-87-3 3,7-dimethyl-2E,6-octadien-1-yl acetate 
• 24034-73-9 Geranylgeraniol 
• 53254-60-7 3,7-dimethyl-1-(p-toluenesulfonyl)-2(E),6-octadiene 
• 33569-79-8 (E,E,E,E,E,E,E)-3,7,11,15,19,23,27,31-octamethyldotriaconta-2,6,10,14,18,22,26,30-octaen-1-ol 
• 78284-77-2 (2E,6E,10E,14E,18E)-3,7,11,15,19,23-hexamethyl-9-p-tolylsulphonyltetracosa-2,6,10,14,18,22-hexaen-1-ol 
• 37905-03-6 8-hydroxygeranyl acetate 
• 37905-04-7 (2E,6E)-8-bromo-3,7-dimethylocta-2,6-dienyl acetate 
• 50848-64-1 2E,6E,10E-geranylgeranyl bromide 
• 73127-51-2 (2E,6E,10E)-3,7,11,15-tetramethyl-9-[(4-methylphenyl)sulfonyl]hexadeca-2,6,10,14-tetraen-1-yl acetate 
• 71816-56-3 (2E,6E,10E)-3,7,11,15-tetramethyl-9-p-tolylsulphonylhexadeca-2,6,10,14-tetraen-1-ol 
• 68690-47-1 1-methyl-4-{[(2E,6E,10E)-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraen-1-yl]sulfonyl}benzene 

Downstream Products

• 303-97-9 ubiquinone-45 
• 124159-62-2 3,4,5-triiodo-benzoic acid-(3,7,11,15,19,23,27,31,35-nonamethyl-hexatriaconta-2t,6t,10t,14t,18t,22t,26t,30t,34-nonaenyl ester) 
• 15575-04-9 decaprenol 
• 108193-67-5 3,5-dinitro-benzoic acid-(3,7,11,15,19,23,27,31,35-nonamethyl-hexatriaconta-2t,6t,10t,14t,18t,22t,26t,30t,34-nonaenyl ester) 
• 523-39-7 2-methyl-3-((2E,6E,10E,14E,18E,22E,26E,30E)-3,7,11,15,19,23,27,31,35- nonamethylhexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-yl)naphthalene-1,4-dione 
• 52610-77-2 solanesyl bromide 
• 65955-43-3 2-Chloro-3-methoxy-6-methyl-5-((2E,6E,10E,14E,18E,22E,26E,30E)-3,7,11,15,19,23,27,31,35-nonamethyl-hexatriaconta-2,6,10,14,18,22,26,30,34-nonaenyl)-[1,4]benzoquinone 
• 65955-42-2 2-Bromo-3-methoxy-6-methyl-5-((2E,6E,10E,14E,18E,22E,26E,30E)-3,7,11,15,19,23,27,31,35-nonamethyl-hexatriaconta-2,6,10,14,18,22,26,30,34-nonaenyl)-[1,4]benzoquinone 
• 17943-91-8 5-Hydroxy-2,3-dimethoxy-6-solanesyl-1,4-benzochinon 
• 944936-30-5 1-[(2E,6E,10E,14E,18E,22E,26E,30E,34E)-5-(4-chlorophenylsulfonyl)-3,7,11,15,19,23,27,31,35,39-decamethyltetraconta-2,6,10,14,18,22,26,30,34,38-decaenyl]-3,4-dimethoxy-2,5-bis(methoxymethoxy)-6-methylbenzene 
• 944936-29-2 1-chloro-4-[(2E,6E,10E,14E,18E,22E,26E,30E)-3,7,11,15,19,23,27,31,35-nonamethylhexatriaconta-2,6,10,14,18,22,26,30,34-nonaenylsulfonyl]benzene 
• 303-98-0 ubidecarenone 
• 64634-91-9 1-[(2E,6E,10E,14E,18E,22E,26E,30E,34E)-3,7,11,15,19,23,27,31,35,39-decamethyltetraconta-2,6,10,14,18,22,26,30,34,38-decaen-1-yl]-3,4-dimethoxy-2,5-bis(methoxymethoxy)-6-methylbenzene 
• 94828-17-8 (2'E,6'E,10'E,14'E,18'E,22'E,26'E,30'E,34'E,38'E)-1-(3',7',11',15',19',23',27',31',35',39'-decamethyltetraconta-2',6',10',14',18',22',26',30',34',38'-decaenyl)-6-methyl-2,3,4,5-tetramethoxybenzene 

Relevant articles and documents

β,γ-dihydropolyprenyl alcohol derivatives and pharmaceutical composition containing a polyprenyl compound

A β,γ-dihydropolyprenyl alcohol derivative having the formula: STR1 wherein n is an integer of 5 to 7 and R is hydrogen, a lower alkyl group or an aliphatic or aromatic acyl group, is new and useful as a phylactic agent against human and animal infectious diseases. Other disclosed polyprenyl compounds are also useful as such agents.

Stereoselective Synthesis of Solanesol and all-trans-Decaprenol

Allylic p-tolyl sulphonates (5), (14), and (16) couple with allylic bromide (7) and geranyl bromide to produce regio- and stereo-chemically pure 1,5-diene systems.The coupling of all-trans-ω-bromogeranyl acetate (7) with geranyl p-tolyl sulphone (5) and higher isoprenologues (21), (24), and (27), followed by reductive elimination of p-tolylsulphonyl group, furnishes a stereoselective synthesis of all-trans-polyprenols (3), (23), (26), and decaprenol (1b).Solanesol (1a) was synthesised using trans-4-chloroprenyl acetate (29) instead of (7).

Hypertension treating agent containing polyprenyl alcohol

This invention relates to a hypertension treating agent comprising a polyprenyl alcohol or an ester thereof of the general formula: STR1 wherein n represents an integer of 7-10 and A represents a group of the general formula: STR2 in which a and b each represent hydrogen or they may form a bond, or STR3 in which R represents hydrogen or --COR', R' being a saturated or unsaturated aliphatic hydrocarbon group of 1-17 carbon atoms; cyclohexyl group; unsubstituted phenyl group or phenyl group substituted with a halogen atom or a lower alkoxy group; (halogen atom-substituted phenoxy)-lower alkyl group; or pyridyl group.