Nootkatone

Nootkatone

Names
IUPAC name 4α,5α-Eremophila-1(10),11-dien-2-one
Systematic IUPAC name (4R,4aS,6R)-4,4a-Dimethyl-6-(prop-1-en-2-yl)-4,4a,5,6,7,8-hexahydronaphthalen-2(3H)-one
Other names (+)-nootkatone
Identifiers
CAS Number	4674-50-4 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:81377 N
ChEMBL	ChEMBL446299 Y
ChemSpider	1064812 Y
ECHA InfoCard	100.022.840
KEGG	C17914 Y
PubChem CID	1268142
UNII	IZ2Y119N4J Y
CompTox Dashboard (EPA)	DTXSID8047050
InChI InChI=1S/C15H22O/c1-10(2)12-5-6-13-8-14(16)7-11(3)15(13,4)9-12/h8,11-12H,1,5-7,9H2,2-4H3/t11-,12-,15+/m1/s1 Y Key: WTOYNNBCKUYIKC-JMSVASOKSA-N Y InChI=1/C15H22O/c1-10(2)12-5-6-13-8-14(16)7-11(3)15(13,4)9-12/h8,11-12H,1,5-7,9H2,2-4H3/t11-,12-,15+/m1/s1 Key: WTOYNNBCKUYIKC-JMSVASOKBQ
SMILES O=C2\C=C1\CC[C@@H](C(=C)C)C[C@@]1(C)[C@H](C)C2
Properties
Chemical formula	C15H22O
Molar mass	218.340 g·mol−1
Appearance	Clear or white crystals, impure samples appear as a viscous yellow liquid
Density	0.968 g/mL
Melting point	36 °C (97 °F; 309 K)
Boiling point	170 °C (338 °F; 443 K)
Solubility in water	Insoluble in water, very soluble in ethanol, dichloromethane, ethyl acetate, soluble in hexanes
Hazards
GHS labelling:[1]
Pictograms
Signal word	Warning
Hazard statements	H317
Precautionary statements	P280
Flash point	~ 100 °C (212 °F; 373 K)
Related compounds
Related terpenes	Valencene
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Nootkatone is an organic compound, a sesquiterpenoid, which means that it is a C15 derivative that also contains an oxygen-containing functional group (a ketone). It is the most valuable aroma compound of grapefruit.^[2] Nootkatone was originally isolated from the wood of the Alaskan yellow cedar, Cupressus nootkatensis. The species name, nootkatensis, is derived from the language of the Nuu-Chah-Nulth people of Canada (formerly referred to as the Nootka people).^[3]