Curzerene

Curzerene
Names
	IUPAC name (6S)-6-Ethenyl-3,6-dimethyl-5-prop-1-en-2-yl-5,7-dihydro-4H-1-benzofuran
	Other names Isogermafuren; Isofuranogermacrene
Identifiers
3D model (JSmol)	Interactive image;
ChemSpider	4475318;
PubChem CID	5316217;
	InChI InChI=1S/C15H20O/c1-6-15(5)8-14-12(11(4)9-16-14)7-13(15)10(2)3/h6,9,13H,1-2,7-8H2,3-5H3/t13?,15-/m1/s1 Key: HICAMHOOTMOHPA-AWKYBWMHSA-N;
	SMILES CC1=COC2=C1CC([C@](C2)(C)C=C)C(=C)C;
Properties
Chemical formula	C15H20O
Molar mass	216.324 g·mol−1
Melting point	65.3 °C estimated
Boiling point	282.8±40.0 °C estimated
Solubility in water	Poorly soluble in water
Hazards
Flash point	117.50 °C
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Curzerene is a volatile, aromatic terpenoid found in many herbs and spices, such as Curcuma zeodaria.^[2] It is a bioactive isolate of Caribbean corals^[3] and is also found in myrrh.^[4] More specifically it has been found to make up a significant portion - 12.97% - of the smoke produced from burning Commiphora myrrha oleo gum resin.^[5] It is also a major component of myrrh oil, which has been shown in vitro to possess anti-inflammatory properties at sub-toxic by inhibiting the production of the inflammatory cytokine IL-6 by human gingival fibroblasts. Anecdotal evidence exists to support the anti-inflammatory effect of myrrh oil.^[6]

Curzerene represents 13.7% of the essential oil extracted from Smyrnium olusatrum, which has demonstrated significant antimicrobial activity in vitro.^[7]

References

^ "KNApSAcK Metabolite Information - C00012040". www.knapsackfamily.com.
^ PubChem. "Curzerene". pubchem.ncbi.nlm.nih.gov. Retrieved 2020-02-28.
^ Roussis, V; Vagias, C; Tsitsimpikou, C; Diamantopoulou, N (2000). "Chemical variability of the volatile metabolites from the Caribbean corals of the genus Gorgonia". Zeitschrift für Naturforschung C. 55 (5–6): 431–41. doi:10.1515/znc-2000-5-620. PMID 10928556. S2CID 201281707.
^ Hanus, Lumir O.; Rezanka, Tomas; Dembitsky, Valery M.; Moussaieff, Arieh (2005). "Myrrh - Commiphora Chemistry". Biomedical Papers. 149 (1): 3–28. doi:10.5507/bp.2005.001. PMID 16170385.
^ Ljaljević Grbić, Milica; Unković, Nikola; Dimkić, Ivica; Janaćković, Peđa; Gavrilović, Milan; Stanojević, Olja; Stupar, Miloš; Vujisić, Ljubodrag; Jelikić, Aleksa; Stanković, Slaviša; Vukojević, Jelena (June 2018). "Frankincense and myrrh essential oils and burn incense fume against micro-inhabitants of sacral ambients. Wisdom of the ancients?". Journal of Ethnopharmacology. 219: 1–14. doi:10.1016/j.jep.2018.03.003. ISSN 0378-8741. PMID 29530608.
^ Tipton, D.A.; Hamman, N.R.; Dabbous, M.Kh. (March 2006). "Effect of myrrh oil on IL-1β stimulation of NF-κB activation and PGE2 production in human gingival fibroblasts and epithelial cells". Toxicology in Vitro. 20 (2): 248–255. doi:10.1016/j.tiv.2005.07.004. ISSN 0887-2333. PMID 16112536.
^ Daroui-Mokaddem, Habiba; Kabouche, Ahmed; Bouacha, Mabrouka; Soumati, Boudjemaa; El-Azzouny, Aida; Bruneau, Christian; Kabouche, Zahia (October 2010). "GC/MS Analysis and Antimicrobial Activity of the Essential Oil of Fresh Leaves of Eucalytus Globulus, and Leaves and Stems of Smyrnium Olusatrum from Constantine (Algeria)". Natural Product Communications. 5 (10): 1934578X1000501. doi:10.1177/1934578x1000501031. ISSN 1934-578X.

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[1] "KNApSAcK Metabolite Information - C00012040". www.knapsackfamily.com.

[2] PubChem. "Curzerene". pubchem.ncbi.nlm.nih.gov. Retrieved 2020-02-28.

[3] Roussis, V; Vagias, C; Tsitsimpikou, C; Diamantopoulou, N (2000). "Chemical variability of the volatile metabolites from the Caribbean corals of the genus Gorgonia". Zeitschrift für Naturforschung C. 55 (5–6): 431–41. doi:10.1515/znc-2000-5-620. PMID 10928556. S2CID 201281707.

[4] Hanus, Lumir O.; Rezanka, Tomas; Dembitsky, Valery M.; Moussaieff, Arieh (2005). "Myrrh - Commiphora Chemistry". Biomedical Papers. 149 (1): 3–28. doi:10.5507/bp.2005.001. PMID 16170385.

[5] Ljaljević Grbić, Milica; Unković, Nikola; Dimkić, Ivica; Janaćković, Peđa; Gavrilović, Milan; Stanojević, Olja; Stupar, Miloš; Vujisić, Ljubodrag; Jelikić, Aleksa; Stanković, Slaviša; Vukojević, Jelena (June 2018). "Frankincense and myrrh essential oils and burn incense fume against micro-inhabitants of sacral ambients. Wisdom of the ancients?". Journal of Ethnopharmacology. 219: 1–14. doi:10.1016/j.jep.2018.03.003. ISSN 0378-8741. PMID 29530608.

[6] Tipton, D.A.; Hamman, N.R.; Dabbous, M.Kh. (March 2006). "Effect of myrrh oil on IL-1β stimulation of NF-κB activation and PGE2 production in human gingival fibroblasts and epithelial cells". Toxicology in Vitro. 20 (2): 248–255. doi:10.1016/j.tiv.2005.07.004. ISSN 0887-2333. PMID 16112536.

[7] Daroui-Mokaddem, Habiba; Kabouche, Ahmed; Bouacha, Mabrouka; Soumati, Boudjemaa; El-Azzouny, Aida; Bruneau, Christian; Kabouche, Zahia (October 2010). "GC/MS Analysis and Antimicrobial Activity of the Essential Oil of Fresh Leaves of Eucalytus Globulus, and Leaves and Stems of Smyrnium Olusatrum from Constantine (Algeria)". Natural Product Communications. 5 (10): 1934578X1000501. doi:10.1177/1934578x1000501031. ISSN 1934-578X.

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