Geraniol

Geraniol

Names
IUPAC name (Z)-3,7-Dimethyl-2,6-octadien-1-ol
Identifiers
CAS Number	106-24-1 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:17447 Y
ChemSpider	13849989 Y
ECHA InfoCard	100.003.071
EC Number	203-377-1
IUPHAR/BPS	2467
PubChem CID	637566
UNII	L837108USY Y
InChI InChI=1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,7,11H,4,6,8H2,1-3H3/b10-7+ Y Key: GLZPCOQZEFWAFX-JXMROGBWSA-N Y InChI=1/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,7,11H,4,6,8H2,1-3H3/b10-7+ Key: GLZPCOQZEFWAFX-JXMROGBWBZ
SMILES CC(=CCC/C(=C/CO)/C)C
Properties
Chemical formula	C10H18O
Molar mass	154.25 g·mol−1
Density	0.889 g/cm3
Melting point	−15 °C (5 °F; 258 K)
Boiling point	230 °C (446 °F; 503 K)
Solubility in water	686 mg/L (20 °C)
Hazards
NFPA 704	1 0 0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Geraniol is a monoterpenoid and an alcohol. It is the primary part of rose oil, palmarosa oil, and citronella oil (Java type). It also occurs in small quantities in geranium, lemon, and many other essential oils. It appears as a clear to pale-yellow oil that is insoluble in water, but soluble in most common organic solvents. It has a rose-like scent and is commonly used in perfumes. It is used in flavors such as peach, raspberry, grapefruit, red apple, plum, lime, orange, lemon, watermelon, pineapple, and blueberry.

Research has shown geraniol to be an effective plant-based mosquito repellent. On the other hand, it can attract bees as it is produced by the scent glands of honey bees to help them mark nectar-bearing flowers and locate the entrances to their hives.

Although geraniol and other flavor compounds are found naturally in well-aged tobacco, geraniol is listed in a 1994 report from cigarette companies as one of the 599 additives to cigarettes to improve their flavor.

The functional group based on geraniol (in essence, geraniol lacking the terminal -OH) is called geranyl. It is important in biosynthesis of other terpenes. It is a by-product of the metabolism of sorbate and, thus, is a very unpleasant contaminant of wine if bacteria are allowed to grow in it.

In acidic solutions, geraniol is converted to the cyclic terpene alpha-terpineol.

Geraniol is classified as D2B (Toxic materials causing other effects) using the Workplace Hazardous Materials Information System (WHMIS). Geraniol is considered a severe eye (and moderate skin) irritant.