Nopol

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
UNII
  • 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)
Insoluble
Solubility in alcohol and oils Soluble
Hazards
GHS labelling:
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)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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.

Synthesis

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

Uses

Nopol is used in the fragrance industry for its balsamic, pine-like scent in soaps, detergents, and household products. 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. Nopol and its derivatives exhibit antifungal, insecticidal, and other bioactivities.

References

  1. 1 2 "Nopol 10-hydroxymethylene-2-pinene". The Good Scents Company. Retrieved February 8, 2026.
  2. 1 2 PubChem. "Nopol". pubchem.ncbi.nlm.nih.gov. Retrieved 2026-02-09.
  3. ↑ J. P. Bain (1946). "Nopol. I. The Reaction of β-Pinene with Formaldehyde". Journal of the American Chemical Society. 68 (4). doi:10.1021/ja01208a032.
  4. ↑ Sumit V. Jadhav, Krishna Mohan Jinka, Hari C. Bajaj (2010). "Synthesis of nopol via Prins condensation of β-pinene and paraformaldehyde catalyzed by sulfated zirconia". Applied Catalysis A: General. 390 (1–2): 158–165. doi:10.1016/j.apcata.2010.10.005.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  5. ↑ M. Selvaraj and P. K. Sinhab (2010). "Highly selective and clean synthesis of nopol over well-ordered mesoporous tin silicate catalysts". New J. Chem. 34: 1921–1929. doi:10.1039/C0NJ00080A.
  6. ↑ Aída Luz Villa de P, Edwin Alarcón, Consuelo Montes de C (2005). "Nopol synthesis over Sn-MCM-41 and Sn-kenyaite catalysts". Catalysis Today. 107–108: 942–948. doi:10.1016/j.cattod.2005.07.049. hdl:10495/9794.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  7. ↑ "Introduction of Nopol and Nopyl acetate". Foreverest Resources Ltd. Retrieved February 8, 2026.
  8. ↑ Surburg, Horst; Panten, Johannes (2016). Common fragrance and flavor materials: preparation, properties and uses (6 ed.). Weinheim: Wiley-VCH Verlag GmbH & Co. KGaA. ISBN 978-3-527-33160-4.
  9. ↑ Opdyke, D. L. J. (2013-10-22). Monographs on Fragrance Raw Materials: A Collection of Monographs Originally Appearing in Food and Cosmetics Toxicology. Elsevier. ISBN 978-1-4831-4797-0.
  10. ↑ Ming Chen, Wen-Gui Duan, Gui-Shan Lin, Zhong-Tian Fan, Xiu Wang (2021). "Synthesis, Antifungal Activity, and 3D-QSAR Study of Novel Nopol-Derived 1,3,4-Thiadiazole-Thiourea Compounds". Molecules. 6 (6): 1708. doi:10.3390/molecules26061708. PMC 8003325.{{cite journal}}: CS1 maint: multiple names: authors list (link)