Menthyl nicotinate

Last updated
Menthyl nicotinate
Menthyl nicotinate-molecule.svg
MenthylNicotinate ball and stick.png
MenthylNicotinate space-filling.png
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
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.049.975 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 254-991-1
PubChem CID
  • 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
  • CC(C)C1CCC(C)CC1OC(=O)C1=CN=CC=C1
Properties
C16H23NO2
Molar mass 261.365 g·mol−1
AppearanceColorless 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)
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:
GHS-pictogram-exclam.svg
Warning
H319
P305+P351+P338
Flash point 165 °C (329 °F; 438 K) @ 101 kPa
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).

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]

Related Research Articles

<span class="mw-page-title-main">Nicotinamide</span> Dietary supplement and medication

Nicotinamide (INN, BAN UK) or niacinamide (USAN US) is a form of vitamin B3 found in food and used as a dietary supplement and medication. As a supplement, it is used orally (swallowed by mouth) to prevent and treat pellagra (niacin deficiency). While nicotinic acid (niacin) may be used for this purpose, nicotinamide has the benefit of not causing skin flushing. As a cream, it is used to treat acne, and has been observed in clinical studies to improve the appearance of aging skin by reducing hyperpigmentation and redness. It is a water-soluble vitamin.

<span class="mw-page-title-main">Peppermint</span> Hybrid flowering plant in the family Lamiaceae

Peppermint is a hybrid species of mint, a cross between watermint and spearmint. Indigenous to Europe and the Middle East, the plant is now widely spread and cultivated in many regions of the world. It is occasionally found in the wild with its parent species.

<span class="mw-page-title-main">Vitamin C</span> Essential nutrient found in citrus fruits and other foods

Vitamin C is a water-soluble vitamin found in citrus and other fruits, berries and vegetables. It is also a generic prescription medication and in some countries is sold as a non-prescription dietary supplement. As a therapy, it is used to prevent and treat scurvy, a disease caused by vitamin C deficiency.

<span class="mw-page-title-main">Vitamin</span> Nutrients required by organisms in small amounts

Vitamins are organic molecules that are essential to an organism in small quantities for proper metabolic function. Essential nutrients cannot be synthesized in the organism in sufficient quantities for survival, and therefore must be obtained through the diet. For example, vitamin C can be synthesized by some species but not by others; it is not considered a vitamin in the first instance but is in the second. Most vitamins are not single molecules, but groups of related molecules called vitamers. For example, there are eight vitamers of vitamin E: four tocopherols and four tocotrienols.

<span class="mw-page-title-main">Niacin</span> Organic compound and a form of vitamin B3

Niacin, also known as nicotinic acid, is an organic compound and a vitamer of vitamin B3, an essential human nutrient. It is produced by plants and animals from the amino acid tryptophan. Niacin is obtained in the diet from a variety of whole and processed foods, with highest contents in fortified packaged foods, meat, poultry, red fish such as tuna and salmon, lesser amounts in nuts, legumes and seeds. Niacin as a dietary supplement is used to treat pellagra, a disease caused by niacin deficiency. Signs and symptoms of pellagra include skin and mouth lesions, anemia, headaches, and tiredness. Many countries mandate its addition to wheat flour or other food grains, thereby reducing the risk of pellagra.

<span class="mw-page-title-main">Vitamin A</span> Essential nutrient

Vitamin A is a fat-soluble vitamin that is an essential nutrient. The term "vitamin A" encompasses a group of chemically related organic compounds that includes retinol, retinyl esters, and several provitamin (precursor) carotenoids, most notably β-carotene (beta-carotene). Vitamin A has multiple functions: growth during embryo development, maintaining the immune system, and healthy vision. For aiding vision specifically, it combines with the protein opsin to form rhodopsin, the light-absorbing molecule necessary for both low-light and color vision.

A nutrient is a substance used by an organism to survive, grow and reproduce. The requirement for dietary nutrient intake applies to animals, plants, fungi and protists. Nutrients can be incorporated into cells for metabolic purposes or excreted by cells to create non-cellular structures such as hair, scales, feathers, or exoskeletons. Some nutrients can be metabolically converted into smaller molecules in the process of releasing energy such as for carbohydrates, lipids, proteins and fermentation products leading to end-products of water and carbon dioxide. All organisms require water. Essential nutrients for animals are the energy sources, some of the amino acids that are combined to create proteins, a subset of fatty acids, vitamins and certain minerals. Plants require more diverse minerals absorbed through roots, plus carbon dioxide and oxygen absorbed through leaves. Fungi live on dead or living organic matter and meet nutrient needs from their host.

<span class="mw-page-title-main">Sunscreen</span> Skin product helping to prevent sunburn

Sunscreen, also known as sunblock, sun lotion or sun cream, is a photoprotective topical product for the skin that helps protect against sunburn and prevent skin cancer. Sunscreens come as lotions, sprays, gels, foams, sticks, powders and other topical products. Sunscreens are common supplements to clothing, particularly sunglasses, sunhats and special sun protective clothing, and other forms of photoprotection.

<span class="mw-page-title-main">Menthol</span> Organic compound used as flavouring and analgesic

Menthol is an organic compound, specifically a monoterpenoid, that occurs naturally in the oils of several plants in the mint family, such as corn mint and peppermint. It is a white or clear waxy crystalline substance that is solid at room temperature and melts slightly above. The main form of menthol occurring in nature is (−)-menthol, which is assigned the (1R,2S,5R) configuration.

<span class="mw-page-title-main">Pellagra</span> Human disease caused by a lack of vitamin B3

Pellagra is a disease caused by a lack of the vitamin niacin (vitamin B3). Symptoms include inflamed skin, diarrhea, dementia, and sores in the mouth. Areas of the skin exposed to friction and radiation are typically affected first. Over time affected skin may become darker, stiffen, peel, or bleed.

<span class="mw-page-title-main">Dihydroxyacetone</span> Chemical compound

Dihydroxyacetone, also known as glycerone, is a simple saccharide with formula C
3
H
6
O
3
.

β-Carotene Red-orange pigment of the terpenoids class

β-Carotene (beta-carotene) is an organic, strongly colored red-orange pigment abundant in fungi, plants, and fruits. It is a member of the carotenes, which are terpenoids (isoprenoids), synthesized biochemically from eight isoprene units and thus having 40 carbons.

<span class="mw-page-title-main">Topical medication</span> Medication applied to body surfaces

A topical medication is a medication that is applied to a particular place on or in the body. Most often topical medication means application to body surfaces such as the skin or mucous membranes to treat ailments via a large range of classes including creams, foams, gels, lotions, and ointments. Many topical medications are epicutaneous, meaning that they are applied directly to the skin. Topical medications may also be inhalational, such as asthma medications, or applied to the surface of tissues other than the skin, such as eye drops applied to the conjunctiva, or ear drops placed in the ear, or medications applied to the surface of a tooth. The word topical derives from Greek τοπικόςtopikos, "of a place".

<span class="mw-page-title-main">Photoaging</span> Ultraviolet light-induced biological development over time

Photoaging or photoageing is a term used for the characteristic changes to skin induced by chronic UVA and UVB exposure. Tretinoin is the best studied retinoid in the treatment of photoaging.

<span class="mw-page-title-main">Copper peptide GHK-Cu</span> Chemical compound

Copper peptide GHK-Cu is a naturally occurring copper complex of the tripeptide glycyl-L-histidyl-L-lysine. The tripeptide has strong affinity for copper(II) and was first isolated from human plasma. It can be found also in saliva and urine.

Vitamin B<sub>3</sub> Class of chemically related vitamers

Vitamin B3, colloquially referred to as niacin, is a vitamin family that includes three forms, or vitamers: niacin (nicotinic acid), nicotinamide (niacinamide), and nicotinamide riboside. All three forms of vitamin B3 are converted within the body to nicotinamide adenine dinucleotide (NAD). NAD is required for human life and people are unable to make it within their bodies without either vitamin B3 or tryptophan. Nicotinamide riboside was identified as a form of vitamin B3 in 2004.

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Laser-assisted drug delivery (LADD) is a drug delivery technique commonly used in the dermatology field that involves lasers. As skin acts as a protective barrier to the environment, the absorption of topical products through the epidermis is limited; thus, different drug delivery modalities have been employed to improve the efficacy of these treatments. The use of lasers in LADD has been shown to enhance the penetration of drugs transdermal, leading to a higher absorption rate, limited systemic effects, and reduced duration of treatment. Although this technique has evolved in the past decade due to its efficacy through scientific research and clinical practice, there remain some limitations regarding the safety aspect that needs to be taken into consideration.

α-Zeacarotene (alpha-zeacarotene) is a form of carotene with a β-ionone ring at one end and a ζ-ionone ring at the opposite end. It is an intermediate in the biosynthesis of various carotenoids and plays a crucial role in the metabolic pathway leading to the production of lycopene and other important carotenoids.

References

  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".
  4. 1 2 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.