Falcarinol is a natural component, an alkylphenol found in some vegetables, such as carrot, ginseng, parsley.
The synthesis process of Falcarinol takes place in different steps:
- Extraction from Natural Sources: Falcarinol is naturally found in several vegetables, including carrots. It can be extracted from these sources through various extraction methods.
- Chemical Synthesis: Falcarinol can also be synthesized chemically. The chemical synthesis of Falcarinol involves the use of a chemical proteomic strategy to identify ALDH2 as a molecular target of falcarinol in cancer cells and confirm enzyme inhibition via covalent alkylation of the active site.
- Biological Synthesis: Another method of producing Falcarinol is through biological synthesis. This method is environmentally safe, cost-effective, dependable, convenient, and easy.
- Homologation: Falcarinol can undergo single or multiple homologations using enantioenriched metal carbenoids. The addition of a suitable enantioenriched lithium or magnesium carbenoid to a boronic ester, with subsequent 1,2-migration, gives a homologated boronic ester with high stereocontrol.
The discovery of its benefits on human health is from 2005, therefore quite recent and stems from a series of studies carried out on animals.
It is present in these plants of the Apiaceae family (Umbrelliferae): anise (Pimpinella anisum), dill (Anethum graveolens), cumin (Carum carvi), coriander (Coriandrum sativum), wild fennel (Foeniculum piperitum), parsley (Petroselinum crispum), celery (Apium graveolens), carrot (Daucus carota), and fennel (Foeniculum vulgare) (1).
Commercial Falcarinol is obtained from harvested plant material and cleaned to remove impurities, then it is ground, extracted using a solvent such as ethanol or methanol, filtered using filter papers or various other filtration methods to separate the liquid extract from the solid plant material. After these preliminary steps, concentration is carried out to remove any excessive solvent by vacuum distillation or rotary evaporation. Depending on the desired level of purity, subsequent purification steps can be employed: crystallisation, chromatography or others. The last step is drying, in which the purified falcarinol is dried under reduced pressure at a low temperature, during which both solvents and impurities are removed.
It is a powerful antioxidant and performs an antitumor function, as this 2014 study (2) shows, also demonstrated anti-inflammatory activity (3).
The same component, but extracted from ginseng, is called panaxynol and it is able to reduce plasma lipid peroxidation induced by oxidative stress (4).
The most relevant studies on this chemical compound have been selected with a summary of their contents:
Falcarinol studies
- Molecular Formula: C17H24O
- Molecular Weight: 244.378 g/mol
- UNII: 8P1DJD416I
- CAS: 21852-80-2
Synonyms:
- Panaxynol
- (3R,9Z)-heptadeca-1,9-dien-4,6-diyn-3-ol
- 1,9-Heptadecadiene-4,6-diyn-3-ol
- 8P1DJD416I
- (3R)-faclarinol
- 1,9Z-heptadecadien-4,6-diyn-3R-ol
- 1,9-Heptadecadiene-4,6-diyn-3-ol,(3R,9Z)-
- (R)-(-)-Falcarinol
- AC1NQY42
- CHEBI:66722
- HSDB 7070
- ZINC8221109
- 9425AF
- LMFA05000689
- SCHEMBL40767
CHEMBL71260
References_________________________________________________________________________
(1) Christensen LP. Aliphatic C(17)-polyacetylenes of the falcarinol type as potential health promoting compounds in food plants of the Apiaceae family. Recent Pat Food Nutr Agric. 2011 Jan;3(1):64-77. doi: 10.2174/2212798411103010064.
Abstract. Many epidemiological studies have provided evidence that a high intake of fruits and vegetables is associated with a reduced risk for the development of cancer and cardiovascular diseases. Fruits and vegetables are known to contain health promoting components such as vitamins, minerals, antioxidants and dietary fibers, however, it is unclear which of these are responsible for the health promoting properties of fruits and vegetables. Aliphatic C(17)-polyacetylenes of the falcarinol type, which occur in common food plants of the Apiaceae family such as carrot, celeriac, parsnip and parsley, have demonstrated interesting bioactivities including antibacterial, antimycobacterial, and antifungal activity as well as anti-inflammatory, anti-platelet-aggregatory, neuritogenic and serotonergic effects. In addition, the cytotoxicity of falcarinol type polyacetylenes towards human cancer cells, bioavailability, and their potential anticancer effect in vivo indicates that these compounds may contribute to the health effects of certain vegetables and hence could be important nutraceuticals. The bioactivity of falcarinol type polyacetylenes occurring in food plants of the Apiaceae family, their possible mode of action and possible health promoting effects are discussed in this review as well as the effect of storage, processing and other factors that can influence the content of these compounds in particular root vegetables and products. Moreover, recent patents on bioactivity of falcarinol type polyacetylenes and inventions making use of this knowledge are presented and discussed.
(2) Tan KW, Killeen DP, Li Y, Paxton JW, Birch NP, Scheepens A. Dietary polyacetylenes of the falcarinol type are inhibitors of breast cancer resistance protein (BCRP/ABCG2). Eur J Pharmacol. 2014 Jan 15;723:346-52. doi: 10.1016/j.ejphar.2013.11.005.
(3) Dawid C, Dunemann F, Schwab W, Nothnagel T, Hofmann T. Bioactive C₁₇-Polyacetylenes in Carrots (Daucus carota L.): Current Knowledge and Future Perspectives. J Agric Food Chem. 2015 Oct 28;63(42):9211-22. doi: 10.1021/acs.jafc.5b04357.
Abstract. C17-polyacetylenes (PAs) are a prominent group of oxylipins and are primarily produced by plants of the families Apiaceae, Araliaceae, and Asteraceae, respectively. Recent studies on the biological activity of polyacetylenes have indicated their potential to improve human health due to anticancer, antifungal, antibacterial, anti-inflammatory, and serotogenic effects. These findings suggest targeting vegetables with elevated levels of bisacetylenic oxylipins, such as falcarinol, by breeding studies. Due to the abundant availability, high diversity of cultivars, worldwide experience, and high agricultural yields, in particular, carrot (Daucus carota L.) genotypes are a very promising target vegetable. This paper provides a review on falcarinol-type C17-polyacetylenes in carrots and a perspective on their potential as a future contributor to improving human health and well-being.
(4) Al-Kuraishy HM, Al-Gareeb AI. Eustress and Malondialdehyde (MDA): Role of Panax Ginseng: Randomized Placebo Controlled Study. Iran J Psychiatry. 2017 Jul;12(3):194-200.
Abstract. Objective: The present study aimed at evaluating the effect of Panax Ginseng on malondialdehyde (MDA) serum levels during eustress on healthy volunteers. Method: In this study, 65 healthy volunteers were recruited from students of a medical school, with the mean age of 22.61±3.63 years. The volunteers were divided into 2 groups: Group A included 35 participants who were treated by Panax Ginseng 500 mg/day, which was regarded as the treated group; group B included 30 participants treated by placebo 500 mg/day, which was regarded as the control group. Baseline data were obtained and then one month after the study, the participants were followed with respect to induction of psychological stress through daily psychomotor performance task and visual working memory accuracy testing. Stress was assessed by malondialdehyde (MDA) serum levels. Results: The participants in the control group showed significant increases in MDA serum levels (p = 0.0004), which were related to significant increases in perceived stress scale from p<0.0001, while Panax Ginseng led to significant reduction in MDA serum levels (p<0.01), with significant increase in perceived stress scale (p = 0.02). Conclusion: Panax Ginseng produced significant reduction in oxidative stress and augmented eustress level in healthy volunteers 1 month after therapy.
Falcarinol 
