Nerol

Summary

Nerol is a monoterpenoid alcohol found in many essential oils such as lemongrass and hops. It was originally isolated from neroli oil, hence its name. This colourless liquid is used in perfumery. Like geraniol, nerol has a sweet rose odor but it is considered to be fresher.[1] Esters and related derivatives of nerol are referred to as neryl, e.g., neryl acetate.

Nerol
Skeletal formula of nerol
Ball-and-stick model of the nerol molecule
Names
Preferred IUPAC name
(2Z)-3,7-Dimethylocta-2,6-dien-1-ol
Identifiers
  • 106-25-2 checkY
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:29452 ☒N
ChEMBL
  • ChEMBL452683 checkY
ChemSpider
  • 558917 checkY
ECHA InfoCard 100.003.072 Edit this at Wikidata
KEGG
  • C09871 checkY
  • 643820
UNII
  • 38G5P53250 ☒N
  • DTXSID3026728 Edit this at Wikidata
  • InChI=1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,7,11H,4,6,8H2,1-3H3/b10-7- checkY
    Key: GLZPCOQZEFWAFX-YFHOEESVSA-N checkY
  • 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-YFHOEESVBO
  • OC\C=C(/CC/C=C(/C)C)C
Properties
C10H18O
Molar mass 154.25 g/mol
Density 0.881 g/cm3
Boiling point 224 to 225 °C (435 to 437 °F; 497 to 498 K) at 745 mmHg
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Isomeric with nerol is geraniol, which is trans- or E-isomer. Nerol readily loses water to form a set of C10 compounds called dipentene. Nerol can be synthesized by pyrolysis of beta-pinene, which also affords myrcene. Hydrochlorination of myrcene gives a series of isomeric chlorides.

See also edit

References edit

  1. ^ Karl-Georg Fahlbusch, Franz-Josef Hammerschmidt, Johannes Panten, Wilhelm Pickenhagen, Dietmar Schatkowski, Kurt Bauer, Dorothea Garbe, Horst Surburg "Flavors and Fragrances" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2002. doi:10.1002/14356007.a11_141