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
CAS Number	128-50-7; (−): 35836-73-8;
3D model (JSmol)	Interactive image; (−): Interactive image;
ChEBI	(−): CHEBI:171826;
ChEMBL	ChEMBL257332;
ChemSpider	29138; (−): 1068002;
ECHA InfoCard	100.004.447
EC Number	204-890-3;
PubChem CID	31408; (−): 23619823; (+): 2723711;
CompTox Dashboard (EPA)	DTXSID10861780 ;
	InChI 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;
	SMILES CC1(C2CC1C(=C2)CCO)C; (−): C(CO)C=1[C@]2(C(C)(C)[C@](C2)(CC1);
Properties
Chemical formula	C11H18O
Molar mass	166.264 g·mol−1
Appearance	Colorless viscous liquid
Boiling point	230 °C (446 °F; 503 K)
Solubility in water	Insoluble
Solubility in alcohol and oils	Soluble
Hazards
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H302, H315, H317, H319, H412
Precautionary statements	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):
LD50 (median dose)	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). Infobox references

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.^[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

^ ^a ^b "Nopol 10-hydroxymethylene-2-pinene". The Good Scents Company. Retrieved February 8, 2026.
^ ^a ^b PubChem. "Nopol". pubchem.ncbi.nlm.nih.gov. Retrieved 2026-02-09.
^ 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.
^ 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)
^ 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.
^ 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)
^ "Introduction of Nopol and Nopyl acetate". Foreverest Resources Ltd. Retrieved February 8, 2026.
^ 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.
^ 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.
^ 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)

[thegoodscentscompany-1] "Nopol 10-hydroxymethylene-2-pinene". The Good Scents Company. Retrieved February 8, 2026.

[PubChem-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)

[foreverest-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)

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