Menthyl nicotinate
{{distinguish|Methyl nicotinate}}
{{Chembox
| Name = Menthyl nicotinate
| ImageFile1 = Menthyl nicotinate-molecule.svg
| ImageFile2 = MenthylNicotinate_ball_and_stick.png
| ImageAlt2 = Ball and stick model of menthyl nicotinate molecule
| ImageFile3 = MenthylNicotinate_space-filling.png
| ImageAlt3 = Space-filling model of menthyl nicotinate molecule
| IUPACName = p-Menthan-3-yl pyridine-3-carboxylate
| SystematicName = 5-Methyl-2-(propan-2-yl)cyclohexyl pyridine-3-carboxylate
| OtherNames = {{bulleted list|5-methyl-2-(isopropyl) cyclohexyl nicotinate|Nicotinic acid p-menthan-3-yl ester|3-Pyridinecarboxylicacid, 5-methyl-2-(1-methylethyl)cyclohexyl ester|Menthyl nicotinate}}
| Section1 = {{Chembox Identifiers
| CASNo = 40594-65-8
| CASNo_Ref = [https://chem.nlm.nih.gov/chemidplus/rn/40594-65-8]
| ChemSpiderID = 14685547
| EC_number = 254-991-1
| PubChem = 13773421
| DTXSID = DTXSID60961007
| SMILES = CC(C)C1CCC(C)CC1OC(=O)C1=CN=CC=C1
| 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
}}
| Section2 = {{Chembox Properties
| C=16 | H=23 | N=1 | O=2
| Appearance = Colorless liquid
| Odor = Odorless at room temperature, aromatic minty odor if warmed up
| Density = 1.031 g/mL at 20 °C
| Solubility = Insoluble
| Solubility1 = Soluble in polar oils, ethanol, organic solvents
| LogP = 5.09 @ 20 °C
| MeltingPt=<
| MeltingPtC = -20
| BoilingPtC = 292.23
| BoilingPt_notes= {{cn|date=January 2025}}
| VaporPressure = 10 Pa @ 20 °C
}}
| Section3 = {{Chembox Hazards
| MainHazards = Eye irritant
| GHSPictograms = {{GHS07}}
| GHSSignalWord = Warning
| HPhrases = {{H-phrases|319}}
| PPhrases = {{P-phrases|305+351+338}}
| FlashPtC = 165
| FlashPt_notes = @ 101 kPa
| AutoignitionPtC = 354
| AutoignitionPt_notes= @ 102.3 kPa
}}
}}
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,{{cite web |url=https://echa.europa.eu/it/substance-information/-/substanceinfo/100.049.975 |title=ECHA InfoCard }} personal lubricants and intimate hygiene compositions.US9,144,572 {{cite web |url=http://patft.uspto.gov/netacgi/nph-Parser?d=PALL&p=1&u=%2Fnetahtml%2FPTO%2Fsrchnum.htm&r=1&f=G&l=50&s1=9144572.PN.&OS=PN/9144572&RS=PN/9144572 |title=Compositions and method for the stimulation of the female and male sexual response }}EP2881107B1 {{cite web |url=https://worldwide.espacenet.com/publicationDetails/originalDocument?FT=D&date=20160907&DB=&locale=en_EP&CC=EP&NR=2881107B1&KC=B1&ND=6# |title=Compositions and method for the stimulation of the female and male sexual response }}
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.{{cite journal|journal=Cosmetic Technology|title=Menthyl Nicotinate – High rate of skin absorption and time-release delivery of Vitamin B3 (Niacin)|first1=G. |last1=Segalla |first2=S. |last2=Giardina |first3=G. |last3=Bizzaro |volume=22|issue=2|pages=36–40|date=March–April 2019|url=https://multichem.it/sites/default/files/PDF/CT_2019_22(2)-ENG-web.pdf}}
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.{{cite journal |last1=Benavente |first1=Claudia |last2=Jacobson |first2=Myron |last3=Jacobson |first3=Elaine |title=NAD in Skin: Therapeutic Approaches for Niacin |journal=Current Pharmaceutical Design |date=1 January 2009 |volume=15 |issue=1 |pages=29–38 |doi=10.2174/138161209787185760 |pmid=19149600 }}{{cite journal |last1=Jacobson |first1=Elaine L. |last2=Kim |first2=Hyuntae |last3=Kim |first3=Moonsun |last4=Williams |first4=Joshua D. |last5=Coyle |first5=Donna L. |last6=Coyle |first6=W. Russell |last7=Grove |first7=Gary |last8=Rizer |first8=Ronald L. |last9=Stratton |first9=M. Suzanne |last10=Jacobson |first10=Myron K. |title=A topical lipophilic niacin derivative increases NAD, epidermal differentiation and barrier function in photodamaged skin |journal=Experimental Dermatology |date=June 2007 |volume=16 |issue=6 |pages=490–499 |doi=10.1111/j.1600-0625.2007.00553.x |pmid=17518989 }}
Niacin has also been used and tested for the purpose of enhancing detoxification by removing skin lipid-stored xenobiotics.{{cite journal |last1=Prousky |first1=Jonathan |title=Niacin for Detoxification: A Little-known Therapeutic Use |journal=Journal of Orthomolecular Medicine |date=January 2011 |volume=26 |issue=2 |pages=85–92 |url=https://www.researchgate.net/publication/269929175}}{{cite journal |last1=Schnare |first1=David W. |last2=Ben |first2=Max |last3=Shields |first3=Megan G. |title=Body Burden Reductions of PCBs, PBBs and Chlorinated Pesticides in Human Subjects |journal=Ambio |date=1984 |volume=13 |issue=5/6 |pages=378–380 |jstor=4313080 }}{{cite journal |last1=Dahlgren |first1=James |last2=Cecchini |first2=Marie |last3=Takhar |first3=Harpreet |last4=Paepke |first4=Olaf |title=Persistent organic pollutants in 9/11 world trade center rescue workers: reduction following detoxification |journal=Chemosphere |date=October 2007 |volume=69 |issue=8 |pages=1320–1325 |doi=10.1016/j.chemosphere.2006.05.127 |pmid=17234251 }}{{cite book |last1=Hoffer |first1=Abram |last2=Saul |first2=Andrew W. |last3=Foster |first3=Harold D. |title=Niacin: the real story |date=2015 |publisher=Basic Health |pages=154–155 |isbn=9781591202752 |language=English}}
In vitro testing has evidenced menthyl nicotinate's fast skin absorption kinetics and slow percutaneous delivery of niacin.
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.{{cn|date=January 2025}} Results indicate that menthyl nicotinate significantly enhances skin barrier function.{{cite journal |last1=Segalla |first1=G. |last2=Giardina |first2=S. |last3=Bizzaro |first3=G. |title=Nicomenthyl: transcutaneous niacin delivery and antipollution, detox, antioxidant efficacy |journal=Cosmetic Technology |date=September–October 2018 |volume=21 |issue=5 |pages=28–34 |url=https://multichem.it/sites/default/files/inline-images/CT_5-ENG-web.pdf}}{{dead link|date=January 2025}}
References
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