Nopol

Chemical compound From Wikipedia, the free encyclopedia

Nopol is a semi-synthetic bicyclic monoterpenoid alcohol with the molecular formula C11H18O. It is a colorless viscous liquid at room temperature. Nopol has a woody, camphoraceous odor and is used in fragrances and flavorings. As a chiral compound, it can exist in either of two enantiomeric forms, (−)-nopol and (+)-nopol.

Quick facts Names, Identifiers ...
Nopol
(−)-Nopol
Names
IUPAC name
2-(6,6-Dimethylbicyclo[3.1.1]hept-2-en-2-yl)ethanol
Other names
  • Nopyl alcohol
  • 6,6-Dimethyl-2-norpinene-2-ethanol
  • 10-Hydroxymethylene-2-pinene
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.004.447 Edit this at Wikidata
EC Number
  • 204-890-3
  • InChI=1S/C11H18O/c1-11(2)9-4-3-8(5-6-12)10(11)7-9/h3,9-10,12H,4-7H2,1-2H3
    Key: ROKSAUSPJGWCSM-UHFFFAOYSA-N
  • (−): InChI=1S/C11H18O/c1-11(2)9-4-3-8(5-6-12)10(11)7-9/h3,9-10,12H,4-7H2,1-2H3/t9?,10-/m0/s1
    Key: ROKSAUSPJGWCSM-AXDSSHIGSA-N
  • CC1(C2CC1C(=C2)CCO)C
  • (−): C(CO)C=1[C@]2(C(C)(C)[C@](C2)(CC1)
Properties
C11H18O
Molar mass 166.264 g·mol−1
Appearance Colorless viscous liquid
Boiling point 230 °C (446 °F; 503 K)[1]
Insoluble
Solubility in alcohol and oils Soluble
Hazards
GHS labelling:[2]
GHS07: Exclamation mark
Warning
H302, H315, H317, H319, H412
P261, P264, P264+P265, P270, P272, P273, P280, P301+P317, P302+P352, P305+P351+P338, P321, P330, P333+P317, P337+P317, P362+P364, P501
Flash point 99 °C (210 °F; 372 K)
Lethal dose or concentration (LD, LC):
890 mg/kg (rat, oral)[2]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Synthesis

Nopol is typically synthesized via the Prins reaction of β-pinene with paraformaldehyde.[3][4] Syntheses using materials such as tin silicate catalysts have also been reported for selective production.[5][6]

Uses

Nopol is used in the fragrance industry for its balsamic, pine-like scent in soaps, detergents, and household products.[1] It serves as an intermediate in the synthesis of pesticides and agrochemicals. Derivatives of nopol, such as nopyl acetate, are employed in perfumery and as fuel additives.[7][8][9] Nopol and its derivatives exhibit antifungal, insecticidal, and other bioactivities.[10]

References

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