Menthyl nicotinate

Menthyl nicotinate
Names
	IUPAC name p-Menthan-3-yl pyridine-3-carboxylate
	Systematic IUPAC name 5-Methyl-2-(propan-2-yl)cyclohexyl pyridine-3-carboxylate
	Other names 5-methyl-2-(isopropyl) cyclohexyl nicotinate; Nicotinic acid p-menthan-3-yl ester; 3-Pyridinecarboxylicacid, 5-methyl-2-(1-methylethyl)cyclohexyl ester; Menthyl nicotinate;
Identifiers
CAS Number	40594-65-8[1];
3D model (JSmol)	Interactive image;
ChemSpider	14685547;
ECHA InfoCard	100.049.975
EC Number	254-991-1;
PubChem CID	13773421;
CompTox Dashboard (EPA)	DTXSID60961007;
	InChI InChI=1/C16H23NO2/c1-11(2)14-7-6-12(3)9-15(14)19-16(18)13-5-4-8-17-10-13/h4-5,8,10-12,14-15H,6-7,9H2,1-3H3;
	SMILES CC(C)C1CCC(C)CC1OC(=O)C1=CN=CC=C1;
Properties
Chemical formula	C16H23NO2
Molar mass	261.365 g·mol−1
Appearance	Colorless liquid
Odor	Odorless at room temperature, aromatic minty odor if warmed up
Density	1.031 g/mL at 20 °C
Melting point	< −20 °C (−4 °F; 253 K)
Boiling point	292.23 °C (558.01 °F; 565.38 K)
Solubility in water	Insoluble
Solubility	Soluble in polar oils, ethanol, organic solvents
log P	5.09 @ 20 °C
Vapor pressure	10 Pa @ 20 °C
Hazards
	Occupational safety and health (OHS/OSH):
Main hazards	Eye irritant
	GHS labelling:
Pictograms
Signal word	Warning
Hazard statements	H319
Precautionary statements	P305+P351+P338
Flash point	165 °C (329 °F; 438 K) @ 101 kPa
Autoignition; temperature	354 °C (669 °F; 627 K) @ 102.3 kPa
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Menthyl nicotinate is an organic compound with the formula C₁₆H₂₃NO₂. It is the ester of nicotinic acid (niacin, vitamin B3) and menthol. At room temperature, menthyl nicotinate is a colorless, odorless, viscous liquid.

Being a topical lipophilic niacin derivative, menthyl nicotinate is used in cosmetics and personal care products,^[1] personal lubricants and intimate hygiene compositions.^[2]^[3]

Menthyl nicotinate is rapidly absorbed through the stratum corneum and slowly hydrolyzed by skin esterase into niacin and menthol. Such time-dependent release of niacin and menthol, in an equimolar ratio, prevents the excessive niacin-flush effect that is usually observed with other nicotinates.^[4]

Niacin is a precursor to coenzyme nicotinamide adenine dinucleotide (NAD), which is essential to all cellular processes involved in immune response and DNA-repairing of photodamaged skin cells.^[5]^[6]

Niacin has also been used and tested for the purpose of enhancing detoxification by removing skin lipid-stored xenobiotics.^[7]^[8]^[9]^[10]

In vitro testing has evidenced menthyl nicotinate's fast skin absorption kinetics and slow percutaneous delivery of niacin.^[4]

Its antioxidant, detox, antipollution and protective efficacy against different kinds of damaging agents (UV radiation, oxidizing agents, urban particulates and cigarette smoke) has also been evaluated. Results indicate that menthyl nicotinate significantly enhances skin barrier function.^[11]

References

^ "ECHA InfoCard".
^ US9,144,572 "Compositions and method for the stimulation of the female and male sexual response".
^ EP2881107B1 "Compositions and method for the stimulation of the female and male sexual response".
^ ^a ^b Segalla, G.; Giardina, S.; Bizzaro, G. (March–April 2019). "Menthyl Nicotinate – High rate of skin absorption and time-release delivery of Vitamin B3 (Niacin)" (PDF). Cosmetic Technology. 22 (2): 36–40.
^ Benavente, Claudia; Jacobson, Myron; Jacobson, Elaine (1 January 2009). "NAD in Skin: Therapeutic Approaches for Niacin". Current Pharmaceutical Design. 15 (1): 29–38. doi:10.2174/138161209787185760. PMID 19149600.
^ Jacobson, Elaine L.; Kim, Hyuntae; Kim, Moonsun; Williams, Joshua D.; Coyle, Donna L.; Coyle, W. Russell; Grove, Gary; Rizer, Ronald L.; Stratton, M. Suzanne; Jacobson, Myron K. (June 2007). "A topical lipophilic niacin derivative increases NAD, epidermal differentiation and barrier function in photodamaged skin". Experimental Dermatology. 16 (6): 490–499. doi:10.1111/j.1600-0625.2007.00553.x. PMID 17518989.
^ Prousky, Jonathan (January 2011). "Niacin for Detoxification: A Little-known Therapeutic Use". Journal of Orthomolecular Medicine. 26 (2): 85–92.
^ Schnare, David W.; Ben, Max; Shields, Megan G. (1984). "Body Burden Reductions of PCBs, PBBs and Chlorinated Pesticides in Human Subjects". Ambio. 13 (5/6): 378–380. JSTOR 4313080.
^ Dahlgren, James; Cecchini, Marie; Takhar, Harpreet; Paepke, Olaf (October 2007). "Persistent organic pollutants in 9/11 world trade center rescue workers: reduction following detoxification". Chemosphere. 69 (8): 1320–1325. doi:10.1016/j.chemosphere.2006.05.127. PMID 17234251.
^ Hoffer, Abram; Saul, Andrew W.; Foster, Harold D. (2015). Niacin: the real story. Basic Health. pp. 154–155. ISBN 9781591202752.
^ Segalla, G.; Giardina, S.; Bizzaro, G. (September–October 2018). "Nicomenthyl: transcutaneous niacin delivery and antipollution, detox, antioxidant efficacy" (PDF). Cosmetic Technology. 21 (5): 28–34.

[1] "ECHA InfoCard".

[2] US9,144,572 "Compositions and method for the stimulation of the female and male sexual response".

[3] EP2881107B1 "Compositions and method for the stimulation of the female and male sexual response".

[ct22(2)-4] Segalla, G.; Giardina, S.; Bizzaro, G. (March–April 2019). "Menthyl Nicotinate – High rate of skin absorption and time-release delivery of Vitamin B3 (Niacin)" (PDF). Cosmetic Technology. 22 (2): 36–40.

[5] Benavente, Claudia; Jacobson, Myron; Jacobson, Elaine (1 January 2009). "NAD in Skin: Therapeutic Approaches for Niacin". Current Pharmaceutical Design. 15 (1): 29–38. doi:10.2174/138161209787185760. PMID 19149600.

[6] Jacobson, Elaine L.; Kim, Hyuntae; Kim, Moonsun; Williams, Joshua D.; Coyle, Donna L.; Coyle, W. Russell; Grove, Gary; Rizer, Ronald L.; Stratton, M. Suzanne; Jacobson, Myron K. (June 2007). "A topical lipophilic niacin derivative increases NAD, epidermal differentiation and barrier function in photodamaged skin". Experimental Dermatology. 16 (6): 490–499. doi:10.1111/j.1600-0625.2007.00553.x. PMID 17518989.

[7] Prousky, Jonathan (January 2011). "Niacin for Detoxification: A Little-known Therapeutic Use". Journal of Orthomolecular Medicine. 26 (2): 85–92.

[8] Schnare, David W.; Ben, Max; Shields, Megan G. (1984). "Body Burden Reductions of PCBs, PBBs and Chlorinated Pesticides in Human Subjects". Ambio. 13 (5/6): 378–380. JSTOR 4313080.

[9] Dahlgren, James; Cecchini, Marie; Takhar, Harpreet; Paepke, Olaf (October 2007). "Persistent organic pollutants in 9/11 world trade center rescue workers: reduction following detoxification". Chemosphere. 69 (8): 1320–1325. doi:10.1016/j.chemosphere.2006.05.127. PMID 17234251.

[10] Hoffer, Abram; Saul, Andrew W.; Foster, Harold D. (2015). Niacin: the real story. Basic Health. pp. 154–155. ISBN 9781591202752.

[11] Segalla, G.; Giardina, S.; Bizzaro, G. (September–October 2018). "Nicomenthyl: transcutaneous niacin delivery and antipollution, detox, antioxidant efficacy" (PDF). Cosmetic Technology. 21 (5): 28–34.

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