| Identification | More | [Name]
Solanesol | [CAS]
13190-97-1 | [Synonyms]
3,7,11,15,19,23,27,31,35-NONAMETHYLHEXATRIACONTA-2,6,10,14,18,22,26,30,34-NONAEN-1-OL
SOLANESOL
(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
Solanesol90%
SOLANESOL 90%
(2E,6E,10E,14E,18E,22E,26E,30E,)-3,7,11,15,19,23,27,31,35-Nonamethyl-2,6,10,14,18,22,26,30,34-hexatriacontanonaen-1-ol
Solanesol from tobacco
2,6,10,14,18,22,26,30,34-Hexatriacontanonaen-1-ol, 3,7,11,15,19,23,27,31,35-nonamethyl-, (2E,6E,10E,14E,18E,22E,26E,30E)-
(2E,6E,10E,14E,18E,22E,26E,30E)-3,7,11,15,19,23,27,31,35-Nonamethyl-2,6,10,14,18,22,26,30,34-hexatriacontanonaene-1-ol
Farnesylfarnesylfarnesol | [EINECS(EC#)]
603-532-7 | [Molecular Formula]
C45H74O | [MDL Number]
MFCD00070279 | [Molecular Weight]
631.07 | [MOL File]
13190-97-1.mol |
| Chemical Properties | Back Directory | [Appearance]
Brown Waxy Solid | [Melting point ]
33°C | [Boiling point ]
685.6±24.0 °C(Predicted) | [density ]
0.889±0.06 g/cm3(Predicted) | [storage temp. ]
−20°C
| [solubility ]
Chloroform (Slightly), Ethyl Acetate (Slightly) | [form ]
Solid | [pka]
14.42±0.10(Predicted) | [color ]
Off-White to Brown Waxy to | [Stability:]
Stable, but may be heat sensitive-store cold. Combustible. Incompatible with strong oxidizing agents. | [Usage]
A high molecular weight isoprenoid alcohol isolated from tobacco leaf | [Detection Methods]
HPLC(RID), NMR | [Merck ]
8703 | [InChIKey]
AFPLNGZPBSKHHQ-MEGGAXOGSA-N | [LogP]
16.149 (est) | [CAS DataBase Reference]
13190-97-1(CAS DataBase Reference) | [EPA Substance Registry System]
13190-97-1(EPA Substance) |
| Safety Data | Back Directory | [Safety Statements ]
24/25 | [WGK Germany ]
3
| [RTECS ]
MP5366666
| [HS Code ]
29052900 | [Toxicity]
mouse,LD50,intraperitoneal,> 4gm/kg (4000mg/kg),United States Patent Document. Vol. #4221810, |
| Material Safety Data Sheet(MSDS) | Back Directory | [msds information]
3,7,11,15,19,23,27,31,35-Nonamethylhexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-ol(13190-97-1).msds |
| Questions And Answer | Back Directory | [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 chemicalbook 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.
| [Chemical Properties]
It is pale yellow powder. It is insoluble in water, slightly soluble in methanol, ethanol and soluble in acetone, chloroform and hexane; It has the m.p. > 33 ℃
| [Uses]
It is an important raw material for the synthesis of coenzyme Q10. The coenzyme Q10 can be acted as the activator of the human cell respiration and metabolism and the immune enhancer of the body.
It can be acted as the intermediate of coenzyme Q10 and vitamin K2. C45 class isopentenol is the most surplus fat in the tobacco leaf and is a important precursor of the tumorigenicity poly nuclear aromatic hydrocarbons in the tobacco.
It is an important pharmaceutical intermediate. It has anti-ulcer and anti-tumor property.
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| Hazard Information | Back Directory | [Definition]
ChEBI: A nonaprenol that is hexatriaconta-2,6,10,14,18,22,26,30,34-nonaen-1-ol substituted by 9 methyl groups at positions 3, 7, 11, 15, 19, 23, 27, 31 and 35 (the all-trans0stereoisomer). |
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