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]
^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".
^ abSegalla, 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. ISBN9781591202752.
menthyl, nicotinate, organic, compound, with, formula, c16h23no2, ester, nicotinic, acid, niacin, vitamin, menthol, room, temperature, menthyl, nicotinate, colorless, odorless, viscous, liquid, namesiupac, name, menthan, pyridine, carboxylatesystematic, iupac,. 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 Menthyl nicotinate NamesIUPAC name p Menthan 3 yl pyridine 3 carboxylateSystematic IUPAC name 5 Methyl 2 propan 2 yl cyclohexyl pyridine 3 carboxylateOther names 5 methyl 2 isopropyl cyclohexyl nicotinateNicotinic acid p menthan 3 yl ester3 Pyridinecarboxylicacid 5 methyl 2 1 methylethyl cyclohexyl esterMenthyl nicotinateIdentifiersCAS Number 40594 65 8 1 3D model JSmol Interactive imageChemSpider 14685547ECHA InfoCard 100 049 975EC Number 254 991 1PubChem CID 13773421CompTox Dashboard EPA DTXSID60961007InChI 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 3H3SMILES CC C C1CCC C CC1OC O C1 CN CC C1PropertiesChemical formula C 16H 23N O 2Molar mass 261 365 g mol 1Appearance Colorless liquidOdor Odorless at room temperature aromatic minty odor if warmed upDensity 1 031 g mL at 20 CMelting point lt 20 C 4 F 253 K Boiling point 292 23 C 558 01 F 565 38 K Solubility in water InsolubleSolubility Soluble in polar oils ethanol organic solventslog P 5 09 20 CVapor pressure 10 Pa 20 CHazardsOccupational safety and health OHS OSH Main hazards Eye irritantGHS labelling PictogramsSignal word WarningHazard statements H319Precautionary statements P305 P351 P338Flash point 165 C 329 F 438 K 101 kPaAutoignitiontemperature 354 C 669 F 627 K 102 3 kPaExcept where otherwise noted data are given for materials in their standard state at 25 C 77 F 100 kPa Infobox references 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 edit 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 Retrieved from https en wikipedia org w index php title Menthyl nicotinate amp oldid 1195697940, wikipedia, wiki, book, books, library,
