# Coumarin derivatives

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"Coumarins" redirects here. For the class of anticoagulants and rodenticides specifically, see [4-Hydroxycoumarins](/source/4-Hydroxycoumarins). For the parent compound, see [Coumarin](/source/Coumarin).

**Coumarin derivatives** are [derivatives](/source/Derivative_(chemistry)) of [coumarin](/source/Coumarin) and are considered [phenylpropanoids](/source/Phenylpropanoids).[1] Among the most important derivatives are the [4-hydroxycoumarins](/source/4-hydroxycoumarins), which exhibit [anticoagulant](/source/Anticoagulant) properties, a characteristic not present for coumarin itself.

Some naturally occurring coumarin derivatives include [umbelliferone](/source/Umbelliferone) (7-hydroxycoumarin), [aesculetin](/source/Aesculetin) (6,7-dihydroxycoumarin), [herniarin](/source/Herniarin) (7-methoxycoumarin), [psoralen](/source/Psoralen) and [imperatorin](/source/Imperatorin).

4-Phenylcoumarin is the backbone of the [neoflavones](/source/Neoflavones), a type of neoflavonoids.

Coumarin-pyrazole hybrids have been synthesized from hydrazones, carbazones and thiocarbazones via Vilsmeier Haack formylation reaction. Whereas, coumarin-pyridine hybrids have been prepared from the [Knoevenagel condensation](/source/Knoevenagel_condensation) of pyridylacetontriles with substituted [salicylaldehydes](/source/Salicylaldehyde).[2]

Compounds derived from coumarin are also called **coumarins** or **coumarinoids**; this family includes:

- [brodifacoum](/source/Brodifacoum)[3][4]
- [bromadiolone](/source/Bromadiolone)[5]
- [difenacoum](/source/Difenacoum)[6]
- [auraptene](/source/Auraptene)
- [ensaculin](/source/Ensaculin)
- [phenprocoumon](/source/Phenprocoumon) (Marcoumar)
- [PSB-SB-487](/source/PSB-SB-487)
- [PSB-SB-1202](/source/PSB-SB-1202)
- [scopoletin](/source/Scopoletin) can be isolated from the bark of *Shorea pinanga*[7]
- [warfarin](/source/Warfarin) (Coumadin)

Coumarin is transformed into the natural [anticoagulant](/source/Anticoagulant) [dicoumarol](/source/Dicoumarol) by a number of species of [fungi](/source/Fungus).[8] This occurs as the result of the production of [4-hydroxycoumarin](/source/4-hydroxycoumarin), then further (in the presence of naturally occurring [formaldehyde](/source/Formaldehyde)) into the actual anticoagulant [dicoumarol](/source/Dicoumarol), a fermentation product and [mycotoxin](/source/Mycotoxin). Dicoumarol was responsible for the bleeding disease known historically as "[sweet clover](/source/Sweet_clover) disease" in cattle eating moldy sweet clover [silage](/source/Silage).[8][9] In [basic research](/source/Basic_research), preliminary evidence exists for coumarin having various biological activities, including [anti-inflammatory](/source/Anti-inflammatory), [anti-tumor](/source/Anti-tumor), [antibacterial](/source/Antibacterial), and [antifungal](/source/Antifungal) properties, among others.[8]

## Uses

### Medicine

Warfarin – a coumarin – with [brand name](/source/Brand_name), *Coumadin*, is a prescription drug used as an anticoagulant to inhibit formation of blood clots, and so is a [therapy](/source/Therapy) for [deep vein thrombosis](/source/Deep_vein_thrombosis) and [pulmonary embolism](/source/Pulmonary_embolism).[10][11][12] It may be used to prevent recurrent blood clot formation from [atrial fibrillation](/source/Atrial_fibrillation), [thrombotic stroke](/source/Thrombotic_stroke), and [transient ischemic attacks](/source/Transient_ischemic_attack).[12]

Coumarins have shown some evidence of biological activity and have limited approval for few medical uses as pharmaceuticals, such as in the treatment of [lymphedema](/source/Lymphedema).[10][13] Both coumarin and [1,3-indandione](/source/1,3-indandione) derivatives produce a [uricosuric](/source/Uricosuric) effect, presumably by interfering with the [renal tubular](/source/Nephron) reabsorption of [urate](/source/Urate).[14]

### Laser dyes

Arising from tunable intramolecular charge transfer (ICT) properties within the molecule, coumarins have found purpose as dyes and stains, particularly those featuring electron-donating substituents at the 7-position, which can be used to enhance this behavior. Coumarin dyes are extensively used as [gain media](/source/Gain_medium) in blue-green tunable organic [dye lasers](/source/Dye_lasers).[15][16][17] Among the various coumarin [laser dyes](/source/Laser_dye) are coumarins 480, 490, 504, 521, 504T, and 521T.[17] Coumarin tetramethyl laser dyes offer wide tunability and high laser gain,[18][19] and they are also used as active medium in coherent [OLED](/source/OLED) emitters.[20][15][16][17] and as a [sensitizer](/source/Photosensitizer) in older [photovoltaic](/source/Photovoltaic) technologies.[21]

## References

1. Jacobowitz, Joseph R. & Weng, Jing-Ke (2020-04-29). "Exploring Uncharted Territories of Plant Specialized Metabolism in the Postgenomic Era". *[Annual Review of Plant Biology](/source/Annual_Review_of_Plant_Biology)*. **71** (1): 631–658. [Annual Reviews](/source/Annual_Reviews_(publisher)). [doi:10.1146/annurev-arplant-081519-035634](https://doi.org/10.1146/annurev-arplant-081519-035634). [ISSN 1543-5008](https://www.worldcat.org/issn/1543-5008). [PMID 32176525](https://pubmed.ncbi.nlm.nih.gov/32176525). [S2CID 212740956](https://api.semanticscholar.org/CorpusID:212740956)

1. Burden, Thomas J.; Fernandez, Kathryn P. R.; Kagoro, Mary; Eastwood, Jonathan B.; Tanner, Theo F. N.; Whitwood, Adrian C.; Clark, Ian P.; Towrie, Michael; Krieger, Jean-Philippe; Lynam, Jason M.; Fairlamb, Ian J. S. (2023). ["Coumarin C−H Functionalization by Mn(I) Carbonyls: Mechanistic Insight by Ultra-Fast IR Spectroscopic Analysis"](https://onlinelibrary.wiley.com/doi/abs/10.1002/chem.202203038). *Chemistry – A European Journal*. **29** (25). [doi:10.1002/chem.202203038](https://doi.org/10.1002/chem.202203038). [ISSN 1521-3765](https://www.worldcat.org/issn/1521-3765). [PMC 10947090](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10947090). [PMID 36625067](https://pubmed.ncbi.nlm.nih.gov/36625067)

1. International Programme on Chemical Safety. ["Brodifacoum (pesticide data sheet)"](http://www.inchem.org/documents/pds/pds/pest57_e.htm). [Archived](https://web.archive.org/web/20061209133155/http://inchem.org/documents/pds/pds/pest57_e.htm) 2006-12-09 at the Wayback Machine. Retrieved 2006-12-14.

1. Laposata, M; Van Cott, E. M.; Lev, M. H. (2007). "Case 1-2007—A 40-Year-Old Woman with Epistaxis, Hematemesis, and Altered Mental Status". *New England Journal of Medicine*. **356** (2): 174–82. [doi:10.1056/NEJMcpc069032](https://doi.org/10.1056/NEJMcpc069032). [PMID 17215536](https://pubmed.ncbi.nlm.nih.gov/17215536)

1. International Programme on Chemical Safety. ["Bromadiolone (pesticide data sheet)"](http://www.inchem.org/documents/pds/pds/pest88_e.htm). [Archived](https://web.archive.org/web/20061221043656/http://www.inchem.org/documents/pds/pds/pest88_e.htm) 2006-12-21 at the Wayback Machine. Retrieved 2006-12-14.

1. International Programme on Chemical Safety. ["Difenacoum (health and safety guide)"](http://www.inchem.org/documents/hsg/hsg/hsg095.htm). Retrieved 2006-12-14.

1. Syah, Y. M. et al. (2009). "A modified oligostilbenoid, diptoindonesin C, from *Shorea pinanga* Scheff". *Natural Product Research*. **23** (7): 591–594. [doi:10.1080/14786410600761235](https://doi.org/10.1080/14786410600761235). [PMID 19401910](https://pubmed.ncbi.nlm.nih.gov/19401910). [S2CID 20216115](https://api.semanticscholar.org/CorpusID:20216115)

1. Venugopala, K. N.; Rashmi, V; Odhav, B (2013). "Review on Natural Coumarin Lead Compounds for Their Pharmacological Activity". *BioMed Research International*. **2013**: 1–14. [doi:10.1155/2013/963248](https://doi.org/10.1155/2013/963248). [PMC 3622347](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3622347). [PMID 23586066](https://pubmed.ncbi.nlm.nih.gov/23586066)

1. Bye, A. & King, H. K. (1970). "The biosynthesis of 4-hydroxycoumarin and dicoumarol by *Aspergillus fumigatus* Fresenius". *Biochemical Journal*. **117** (2): 237–45. [doi:10.1042/bj1170237](https://doi.org/10.1042/bj1170237). [PMC 1178855](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1178855). [PMID 4192639](https://pubmed.ncbi.nlm.nih.gov/4192639)

1. ["Coumarin"](https://pubchem.ncbi.nlm.nih.gov/compound/323). PubChem, National Library of Medicine, US National Institutes of Health. 4 April 2019. Retrieved 13 April 2019.

1. ["Coumarins and indandiones"](https://www.drugs.com/drug-class/coumarins-and-indandiones.html). Drugs.com. 2016. Retrieved 24 December 2016.

1. ["Warfarin"](https://www.drugs.com/ppa/warfarin.html). Drugs.com. 7 March 2019. Retrieved 13 April 2019.

1. Farinola, N. & Piller, N. (June 1, 2005). "Pharmacogenomics: Its role in re-establishing coumarin as treatment for lymphedema". *Lymphatic Research and Biology*. **3** (2): 81–86. [doi:10.1089/lrb.2005.3.81](https://doi.org/10.1089/lrb.2005.3.81). [PMID 16000056](https://pubmed.ncbi.nlm.nih.gov/16000056)

1. Christensen, Flemming (1964-01-12). "Uricosuric Effect of Dicoumarol". *Acta Medica Scandinavica*. **175** (4): 461–468. [doi:10.1111/j.0954-6820.1964.tb00594.x](https://doi.org/10.1111/j.0954-6820.1964.tb00594.x). [ISSN 0954-6820](https://www.worldcat.org/issn/0954-6820). [PMID 14149651](https://pubmed.ncbi.nlm.nih.gov/14149651)

1. *Dye Lasers*. 3rd ed. Berlin: Springer-Verlag. 1990.

1. *Dye Laser Principles*. New York: Academic. 1990.

1. Duarte, F. J. (2003). "Appendix of Laser Dyes". *Tunable Laser Optics*. New York: Elsevier-Academic.

1. Chen, C. H.; Fox, J. L.; Duarte, F. J. (1988). "Lasing characteristics of new-coumarin-analog dyes: broadband and narrow-linewidth performance". *Appl. Opt.*. **27** (3): 443–445. [Bibcode:1988ApOpt..27..443C](https://ui.adsabs.harvard.edu/abs/1988ApOpt..27..443C). [doi:10.1364/ao.27.000443](https://doi.org/10.1364/ao.27.000443). [PMID 20523615](https://pubmed.ncbi.nlm.nih.gov/20523615)

1. Duarte, F. J.; Liao, L. S.; Vaeth, K. M.; Miller, A. M. (2006). "Widely tunable laser emission using the coumarin 545 tetramethyl dye as gain medium". *J. Opt. A*. **8** (2): 172–174. [Bibcode:2006JOptA...8..172D](https://ui.adsabs.harvard.edu/abs/2006JOptA...8..172D). [doi:10.1088/1464-4258/8/2/010](https://doi.org/10.1088/1464-4258/8/2/010)

1. Duarte, F. J.; Liao, L. S.; Vaeth, K. M. (2005). "Coherence characteristics of electrically excited tandem organic light-emitting diodes". *Opt. Lett.*. **30** (22): 3072–3074. [Bibcode:2005OptL...30.3072D](https://ui.adsabs.harvard.edu/abs/2005OptL...30.3072D). [doi:10.1364/ol.30.003072](https://doi.org/10.1364/ol.30.003072). [PMID 16315725](https://pubmed.ncbi.nlm.nih.gov/16315725)

1. No. 4175982.

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