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;
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) [citation needed]
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,^[2] personal lubricants and intimate hygiene compositions.^[3]^[4]

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.^[5]

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.^[6]^[7]

Niacin has also been used and tested for the purpose of enhancing detoxification by removing skin lipid-stored xenobiotics.^[8]^[9]^[10]^[11]

In vitro testing has evidenced menthyl nicotinate's fast skin absorption kinetics and slow percutaneous delivery of niacin.^[5]

Its antioxidant, antipollution, and protective efficacy against different kinds of damaging agents (UV radiation, oxidizing agents, urban particulates, and cigarette smoke) has also been evaluated.^{[citation needed]} Results indicate that menthyl nicotinate significantly enhances skin barrier function.^[12]^{[dead link‍]}

References

^ [1]
^ "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] [1]

[2] "ECHA InfoCard".

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

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

[ct22(2)-5] 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.

[6] 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.

[7] 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.

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

[9] 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.

[10] 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.

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

[12] 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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