Falcarindiol

{{Chembox

| ImageFile = Falcarindiol.svg

| ImageSize = 200px

| ImageFile2 = Falcarindiol 3D BS.png

| ImageSize2 = 200px

| PIN = (3R,8S,9Z)-Heptadeca-1,9-diene-4,6-diyne-3,8-diol

| OtherNames = cis-Heptadeca-1,9-diene-4,6-diyne-3,8-diol

|Section1={{Chembox Identifiers

| CASNo = 55297-87-5

| CASNo_Ref = {{cascite|correct|}}

| PubChem = 5281148

| ChemSpiderID = 4444588

| ChEMBL = 69018

| SMILES = CCCCCCC/C=C\[C@H](O)C#CC#C[C@H](O)C=C

| InChI = 1/C17H24O2/c1-3-5-6-7-8-9-10-14-17(19)15-12-11-13-16(18)4-2/h4,10,14,16-19H,2-3,5-9H2,1H3/b14-10-/t16-,17+/m1/s1

| InChIKey = QWCNQXNAFCBLLV-YWALDVPYBU

| StdInChI = 1S/C17H24O2/c1-3-5-6-7-8-9-10-14-17(19)15-12-11-13-16(18)4-2/h4,10,14,16-19H,2-3,5-9H2,1H3/b14-10-/t16-,17+/m1/s1

| StdInChIKey = QWCNQXNAFCBLLV-YWALDVPYSA-N

}}

|Section2={{Chembox Properties

| C = 17 | H = 24 | O =2

}}

}}

Falcarindiol is a polyyne found in carrot roots which has antifungal activity.{{cite journal | last1 = Garrod | first1 = B. | title = Cis-heptadeca-1,9-diene-4,6-diyne-3,8-diol, an antifungal polyacetylene from carrot root tissue | journal = Physiological Plant Pathology | year = 1978 | volume = 13 | issue = 2 | pages = 241–246 | doi = 10.1016/0048-4059(78)90039-5 }}{{ cite journal | author = Kemp, M. S. | title = Falcarindiol: An antifungal polyacetylene from Aegopodium podagraria | journal = Phytochemistry | year = 1978 | volume = 17 | issue = 5 | pages = 1002 | doi = 10.1016/S0031-9422(00)88669-0 | bibcode = 1978PChem..17.1002K }} Falcarindiol is the main compound responsible for bitterness in carrots.{{ cite journal | pmid = 12797757 | last1 = Czepa | first1 = A. | last2 = Hofmann | first2 = T. | title = Structural and sensory characterization of compounds contributing to the bitter off-taste of carrots (Daucus carota L.) and carrot puree | journal = Journal of Agricultural and Food Chemistry | year = 2003 | volume = 51 | issue = 13 | pages = 3865–3873 | doi = 10.1021/jf034085+ }} Falcarindiol and other falcarindiol-type polyacetylenes are also found in many other plants of the family Apiaceae, including some commonly used seasonings such as dill and parsley.{{ cite journal |author1=Christensen, L. P. |author2=Brandt, K. | title = Bioactive polyacetylenes in food plants of the Apiaceae family: Occurrence, bioactivity and analysis | journal = Journal of Pharmaceutical and Biomedical Analysis | year = 2006 | volume = 41 | issue = 3 | pages = 683–693 | doi = 10.1016/j.jpba.2006.01.057 | pmid = 16520011 }}

A variety of bioactivities have been reported for falcaridiol and the falcarindiol-type polyacetylenes,{{ cite journal |author1=Jin, H. R. |author2=Zhao, J. |author3=Zhang, Z. |author4=Liao, Y. |author5=Wang, C. Z. |author6=Huang, W. H. |author7=Li, S. P. |author8=He, T. C. |author9=Yuan, C. S. |author10=Du, W. | title = The antitumor natural compound falcarindiol promotes cancer cell death by inducing endoplasmic reticulum stress | journal = Cell Death and Disease | year = 2012 | volume = 3 | issue = 8 | pages = e376 | doi = 10.1038/cddis.2012.122 | pmid = 22914324 | pmc = 3434669 }}{{ cite journal |author1=Wyrembek, P. |author2=Negri, R. |author3=Kaczor, P. |author4=Czyżewska, M. |author5=Appendino, G. |author6=Mozrzymas, J. W. | title = Falcarindiol allosterically modulates GABAergic currents in cultured rat hippocampal neurons | journal = Journal of Natural Products | year = 2012 | volume = 75 | issue = 4 | pages = 610–616 | doi = 10.1021/np2008522 | pmid = 22432736 }}{{cite journal | doi = 10.3389/fphar.2017.00596| doi-access = free| title = The Dietary Constituent Falcarindiol Promotes Cholesterol Efflux from THP-1 Macrophages by Increasing ABCA1 Gene Transcription and Protein Stability| date = 2017| last1 = Wang| first1 = Limei| last2 = Palme| first2 = Veronika| last3 = Schilcher| first3 = Nicole| last4 = Ladurner| first4 = Angela| last5 = Heiss| first5 = Elke H.| last6 = Stangl| first6 = Herbert| last7 = Bauer| first7 = Rudolf| last8 = Dirsch| first8 = Verena M.| last9 = Atanasov| first9 = Atanas G.| journal = Frontiers in Pharmacology| volume = 8| page = 596| pmid = 28919859| pmc = 5585181}}. and because of potential health-promoting metabolic effects these compounds are studied as potential nutraceuticals.{{ cite journal | author = Christensen, L. P. | title = Aliphatic C17-Polyacetylenes of the Falcarinol Type as Potential Health Promoting Compounds in Food Plants of the Apiaceae Family | journal = Recent Patents on Food, Nutrition & Agriculture | year = 2011 | volume = 3 | issue = 1 | pages = 64–77 | doi = 10.2174/2212798411103010064 | pmid = 21114468 }} Falcarindiol is the most-active among several polyynes found in Devil's club (Oplopanax horridus) that inhibit cell proliferation.{{cite journal |journal= J. Ethnopharmacol. |year= 2010 |volume= 132 |issue= 1 |pages= 280–285 |doi= 10.1016/j.jep.2010.08.026 |pmid= 20723598 |title= Hydrophobic constituents and their potential anticancer activities from Devil's Club (Oplopanax horridus Miq.) |last1= Sun |first1= S |last2= Du |first2= GJ |last3= Qi |first3= LW |last4= Williams |first4= S |last5= Wang |first5= CZ |last6= Yuan |first6= CS |pmc= 3050531}}