Viridiflorol

Viridiflorol
Names
	IUPAC name 6β,11-Cyclo-1β,4α,5β,10α-guaian-10-ol
	Systematic IUPAC name (1aR,4S,4aS,7R,7aS,7bS)-1,1,4,7-Tetramethyldecahydro-1H-cyclopropa[e]azulen-4-ol
	Other names (+)-Viridiflorol
Identifiers
CAS Number	552-02-3;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:156228;
ChEMBL	ChEMBL3120647;
ChemSpider	91904;
ECHA InfoCard	100.008.186
EC Number	209-003-3;
PubChem CID	11996452;
UNII	HN71V2CRMY;
CompTox Dashboard (EPA)	DTXSID80881213 ;
	InChI InChI=1S/C15H26O/c1-9-5-6-10-12(9)13-11(14(13,2)3)7-8-15(10,4)16/h9-13,16H,5-8H2,1-4H3/t9-,10+,11-,12-,13-,15+/m1/s1 Key: AYXPYQRXGNDJFU-IMNVLQEYSA-N;
	SMILES C[C@@H]1CC[C@H]2[C@@H]1[C@H]3[C@H](C3(C)C)CC[C@]2(C)O;
Properties
Chemical formula	C15H26O
Molar mass	222.372 g·mol−1
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H315, H319
Precautionary statements	P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, P362
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Viridiflorol is a chemical compound, classified as a sesquiterpenoid, that has been isolated from the essential oils of a variety of plants including Melaleuca quinquenervia^[1] (broad-leaved paperbark), Melaleuca alternifolia^[2] (tea tree), and Allophylus edulis.^[3]

Viridiflorol has shown moderate antibacterial activity against Mycobacterium tuberculosis, the causative agent of tuberculosis, in an in vitro assay. ^[1] It is also produced by the endophytic root fungus Serendipita indica and exhibits antifungal activity against Colletotrichum truncatum ^[4]

References

^ ^a ^b Ireland, B.F.; Hibbert, D.B.; Goldsack, R.J.; Doran, J.C.; Brophy, J.J. (2002). "Chemical variation in the leaf essential oil of Melaleuca quinquenervia (Cav.). It is also produced by the endopytic fungus Serendipita indica S.T. Blake". Biochemical Systematics and Ecology. 30 (5): 457–470. doi:10.1016/s0305-1978(01)00112-0.
^ "Essential oil of Melaleuca, terpene-4-ol (tea tree oil): ISO 4730: 2017 (E)". International Organization for Standardization (ISO), Geneva, Switzerland. 2017. Retrieved 6 March 2019.
^ Trevizan, Lucas Noboru Fatori; Nascimento, Kamilla Felipe do; Santos, Joyce Alencar; Kassuya, Candida Aparecida Leite; Cardoso, Claudia Andrea Lima; Vieira, Maria do Carmo; Moreira, Flora Martinez Figueira; Croda, Julio; Formagio, Anelise Samara Nazari (2016). "Anti-inflammatory, antioxidant and anti- Mycobacterium tuberculosis activity of viridiflorol: The major constituent of Allophylus edulis (A. St.-Hil., A. Juss. & Cambess.) Radlk". Journal of Ethnopharmacology. 192: 510–515. doi:10.1016/j.jep.2016.08.053. PMID 27612433.
^ Ntana, F.; Bhat, W.W.; Johnson, S.R.; Jørgensen, H.J.L.; Collinge, D.B.; Jensen, B.; Hamberger, B. (2021). "A Sesquiterpene Synthase from the Endophytic Fungus Serendipita indica Catalyzes Formation of Viridiflorol". Biomolecules. 11 (6): 898. doi:10.3390/biom11060898. PMC 8234273. PMID 34208762.

[Trevizan-1] Ireland, B.F.; Hibbert, D.B.; Goldsack, R.J.; Doran, J.C.; Brophy, J.J. (2002). "Chemical variation in the leaf essential oil of Melaleuca quinquenervia (Cav.). It is also produced by the endopytic fungus Serendipita indica S.T. Blake". Biochemical Systematics and Ecology. 30 (5): 457–470. doi:10.1016/s0305-1978(01)00112-0.

[2] "Essential oil of Melaleuca, terpene-4-ol (tea tree oil): ISO 4730: 2017 (E)". International Organization for Standardization (ISO), Geneva, Switzerland. 2017. Retrieved 6 March 2019.

[3] Trevizan, Lucas Noboru Fatori; Nascimento, Kamilla Felipe do; Santos, Joyce Alencar; Kassuya, Candida Aparecida Leite; Cardoso, Claudia Andrea Lima; Vieira, Maria do Carmo; Moreira, Flora Martinez Figueira; Croda, Julio; Formagio, Anelise Samara Nazari (2016). "Anti-inflammatory, antioxidant and anti- Mycobacterium tuberculosis activity of viridiflorol: The major constituent of Allophylus edulis (A. St.-Hil., A. Juss. & Cambess.) Radlk". Journal of Ethnopharmacology. 192: 510–515. doi:10.1016/j.jep.2016.08.053. PMID 27612433.

[Ntana-4] Ntana, F.; Bhat, W.W.; Johnson, S.R.; Jørgensen, H.J.L.; Collinge, D.B.; Jensen, B.; Hamberger, B. (2021). "A Sesquiterpene Synthase from the Endophytic Fungus Serendipita indica Catalyzes Formation of Viridiflorol". Biomolecules. 11 (6): 898. doi:10.3390/biom11060898. PMC 8234273. PMID 34208762.

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