Minquartynoic acid
{{Chembox
| Name = Minquartynoic acid
| ImageFile = Minquartynoic acid.svg
| ImageSize = 250px
| ImageAlt =
| IUPACName = (17S)-17-hydroxyoctadeca-9,11,13,15-tetraynoic acid
| OtherNames =
| Section1 = {{Chembox Identifiers
| CASNo = 123154-43-8 (S-Form)
| CASNo_Ref = {{Cascite|changed|CAS}}
| ChemSpiderID = 159656
| DTXSID = DTXSID90153872
| EC_number =
| ChEBI = 542606
| ChEMBL = 487989
| UNII =
| PubChem = 183614
| InChI =
InChI=1S/C18H20O3/c1-17(19)15-13-11-9-7-5-3-2-4-6-8-10-12-14-16-18(20)21/h17,19H,4,6,8,10,12,14,16H2,1H3,(H,20,21)/t17-/m0/s1
| InChIKey = MTWGWIOCIREVRF-KRWDZBQOSA-N
| SMILES = CC(C#CC#CC#CC#CCCCCCCCC(=O)O)O
}}
| Section2 = {{Chembox Properties
| H=20|O=3|C=18
| MolarMass =
| Appearance = grey-yellow needles{{cite book |last1=Gunstone |first1=Frank D. |last2=Harwood |first2=John L. |last3=Padley |first3=Fred B. |title=The Lipid Handbook, Second Edition |date=21 July 1994 |publisher=CRC Press |isbn=978-0-412-43320-7 |page=226 |url=https://books.google.com/books?id=m9J9pTDZEGEC&dq=Minquartynoic+acid&pg=RA1-PA489 |access-date=11 April 2025 |language=en}}
| Density =
| MeltingPtC = 95
| BoilingPtC =
| BoilingPt_ref =
| Solubility =
}}
| Section3 = {{Chembox Hazards
| GHSPictograms =
| GHSSignalWord =
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| FlashPt =
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Minquartynoic acid is an unsaturated, conjugated, and hydroxylated fatty acid containing four triple bonds and belonging to the class of polyyne and alkynoic acids. It was only discovered in 1989.{{cite journal |last1=Gung |first1=Benjamin W. |title=Total synthesis of polyyne natural products |journal=Comptes Rendus. Chimie |date=2009 |volume=12 |issue=3–4 |pages=489–505 |doi=10.1016/j.crci.2008.08.014 |url=https://comptes-rendus.academie-sciences.fr/chimie/articles/10.1016/j.crci.2008.08.014/ |access-date=11 April 2025 |language=fr |issn=1878-1543}} The acid is optically active, but there are conflicting data regarding the rotation of the natural S-isomer.{{cite journal |last1=Rasmussen |first1=Hasse Bonde |last2=Christensen |first2=Søren Brøgger |last3=Kvist |first3=Lars Peter |last4=Kharazmi |first4=Arzalan |last5=Huansi |first5=Andrea Gonzales |title=Absolute Configuration and Antiprotozoal Activity of Minquartynoic Acid |journal=Journal of Natural Products |date=1 September 2000 |volume=63 |issue=9 |pages=1295–1296 |doi=10.1021/np990604k |pmid=11000043 |bibcode=2000JNAtP..63.1295R |url=https://pubs.acs.org/doi/10.1021/np990604k |access-date=11 April 2025 |issn=0163-3864|url-access=subscription }}
Discovery
The acid was initially isolated by R.J. Marles, N.R. Farnsworth and D.A. Neill in 1989 from the stem of the Amazonian tree ''Minquartia guianensis.{{cite book |last1=Nigg |first1=H. N. |last2=Seigler |first2=D. |title=Phytochemical Resources for Medicine and Agriculture |date=29 June 2013 |publisher=Springer Science & Business Media |isbn=978-1-4899-2584-8 |page=145 |url=https://books.google.com/books?id=YxT3BwAAQBAJ&dq=Minquartynoic+acid+1989&pg=PA145 |access-date=11 April 2025 |language=en}}{{cite book |last1=Hostettmann |first1=Kurt |title=Chemistry, Biological and Pharmacological Properties of Medicinal Plants from the Americas |date=19 December 2018 |publisher=Routledge |isbn=978-1-351-46108-5 |url=https://books.google.com/books?id=-XuCDwAAQBAJ&dq=Minquartynoic+acid&pg=PA224 |access-date=11 April 2025 |language=en}}
Natural occurrence
The acid occurs only in small quantities in the bark or twigs of a few plant species, such as Minquartia guianensis, Ochanostachys amentacea,{{cite book |last1=Wiart |first1=Christophe |title=Medicinal Plants in the Asia Pacific for Zoonotic Pandemics, Volume 3: Family Bixaceae to Portulacaceae |date=5 December 2021 |publisher=CRC Press |isbn=978-1-000-47726-9 |page=184 |url=https://books.google.com/books?id=SDlJEAAAQBAJ&dq=Minquartynoic+acid&pg=PA184 |access-date=11 April 2025 |language=en}} and Coula edulis,{{cite journal |last1=Fort |first1=Diana M |last2=King |first2=Steven R |last3=Carlson |first3=Thomas J |last4=Nelson |first4=Susan T |title=Minquartynoic acid from Coula edulis |journal=Biochemical Systematics and Ecology |date=1 June 2000 |volume=28 |issue=5 |pages=489–490 |doi=10.1016/S0305-1978(99)00079-4 |pmid=10725606 |bibcode=2000BioSE..28..489F |url=https://www.sciencedirect.com/science/article/abs/pii/S0305197899000794 |access-date=11 April 2025 |issn=0305-1978|url-access=subscription }} all of the family Olacaceae.
Synthesis
Minquartynoic acid can be synthesized starting from azelaic acid monomethyl ester in a seven-step synthesis.{{cite journal |last1=Gung |first1=Benjamin W. |last2=Dickson |first2=Hamilton |title=Total Synthesis of (−)-Minquartynoic Acid: An Anti-Cancer, Anti-HIV Natural Product |journal=Organic Letters |date=1 July 2002 |volume=4 |issue=15 |pages=2517–2519 |doi=10.1021/ol026145n |pmid=12123365 |url=https://pubs.acs.org/doi/10.1021/ol026145n |access-date=11 April 2025 |issn=1523-7060|url-access=subscription }} Another synthesis of the compound has also been published.{{cite journal |last1=Sabitha |first1=Gowravaram |last2=Reddy |first2=Ch. Srinivas |last3=Yadav |first3=J. S. |title=Total syntheses of the highly potent anti-cancer polyacetylenes, (S)-18-hydroxyminquartynoic acid, (S)-minquartynoic acid and (E)-15,16-dihydrominquartynoic acid |journal=Tetrahedron Letters |date=26 June 2006 |volume=47 |issue=26 |pages=4513–4516 |doi=10.1016/j.tetlet.2006.03.118 |url=https://linkinghub.elsevier.com/retrieve/pii/S0040403906005910 |access-date=11 April 2025 |issn=0040-4039|url-access=subscription }}
An infusion of the acid has been used by Ecuadorian indigenous people to treat intestinal parasitic infections, lung cancer, and tuberculosis; also, it has been applied topically to treat skin irritations and muscle pain.{{cite journal |last1=Marles |first1=Robin J. |last2=Farnsworth |first2=Norman R. |last3=Neill |first3=David A. |title=Isolation Of A Novel Cytotoxic Polyacetylene From A Traditional Anthelmintic Medicinal Plant, Minquartia guianensis |journal=Journal of Natural Products |date=1 March 1989 |volume=52 |issue=2 |pages=261–266 |doi=10.1021/np50062a007 |bibcode=1989JNAtP..52..261M |url=https://pubs.acs.org/doi/abs/10.1021/np50062a007 |access-date=11 April 2025 |issn=0163-3864|url-access=subscription }}
Uses
In in vitro studies, minquartynoic acid was antiviral against HIV and cytotoxic against ten different cancer cell lines, including leukemia cells.{{cite journal |last1=Rashid |first1=Mohammad A. |last2=and Boyd |first2=Michael R. |title=Absolute Stereochemistry and Anti-HIV Activity of Minquartynoic Acid, A Polyacetylene from Ochanostachys amentacea 1a |journal=Natural Product Letters |date=1 January 2001 |volume=15 |issue=1 |pages=21–26 |doi=10.1080/10575630108041253 |pmid=11547419 |url=https://www.tandfonline.com/doi/abs/10.1080/10575630108041253 |access-date=11 April 2025 |issn=1057-5634|url-access=subscription }}{{cite journal |last1=Dembitsky |first1=Valery M. |title=Anticancer activity of natural and synthetic acetylenic lipids |journal=Lipids |date=2006 |volume=41 |issue=10 |pages=883–924 |doi=10.1007/s11745-006-5044-3 |pmid=17180879 |url=https://aocs.onlinelibrary.wiley.com/doi/10.1007/s11745-006-5044-3 |access-date=11 April 2025 |language=en |issn=1558-9307|url-access=subscription }} In other studies, it has shown activity against malaria and Leishmania.