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Viridiflorol

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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-cyclopropaazulen-4-ol
Other names (+)-Viridiflorol
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.008.186 Edit this at Wikidata
EC Number
  • 209-003-3
PubChem CID
UNII
CompTox Dashboard (EPA)
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/s1Key: AYXPYQRXGNDJFU-IMNVLQEYSA-N
SMILES
  • C1CC213(C3(C)C)CC2(C)O
Properties
Chemical formula C15H26O
Molar mass 222.372 g·mol
Hazards
GHS labelling:
Pictograms GHS07: Exclamation mark
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 , 100 kPa). Infobox references
Chemical compound

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 (broad-leaved paperbark), Melaleuca alternifolia (tea tree), and Allophylus edulis.

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

References

  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.
  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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