Glyceryl octyl ascorbic acid

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Glyceryl octyl ascorbic acid
Glyceryl octyl ascorbic acid.svg
Names
IUPAC name
(2R)-2-[(1S)-1,2-dihydroxyethyl]-3-(2,3-dihydroxypropoxy)-4-octoxy-2H-furan-5-one
Other names
3-O-glyceryl-2-O-octyl ascorbic acid; 3-O-(2,3-Dihydroxypropyl)-2-O-octyl-L-ascorbic acid
Identifiers
3D model (JSmol)
PubChem CID
  • InChI=1S/C17H30O8/c1-2-3-4-5-6-7-8-23-16-15(24-11-12(20)9-18)14(13(21)10-19)25-17(16)22/h12-14,18-21H,2-11H2,1H3/t12?,13-,14+/m0/s1
    Key: BZNPYIWZPTYCQH-KFTPUPIBSA-N
  • CCCCCCCCOC1=C([C@H](OC1=O)[C@H](CO)O)OCC(CO)O
Properties
C17H30O8
Molar mass 362.419 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Glyceryl octyl ascorbic acid (GO-VC) is an amphipathic derivative of vitamin C consisting of two ether linkages: a 1-octyl at position 2 and a glycerin at position 3. The chemical name is 2-glyceryl-3-octyl ascorbic acid. The isomer in which these two groups are swapped (2-octyl-3-glyceryl ascorbic acid, OG-VC) is also known. [1]

Contents

It is considered as a new stable amphipathic vitamin C derivative  [ ja ] in the field of aesthetic medicine. [2]

Overview

Vitamin C is rapidly converted to ascorbic acid radicals by UV rays, which causes cytotoxicity and sunburn, [3] but GO-VC improves the stability of conventional vitamin C derivatives, and thus eliminates the problems of these prooxidants.　Water-soluble vitamin C derivatives, such as sodium ascorbyl phosphate (APS), which have been used since the 1990s, have a problem of drying the skin in order to the sebum suppression effect. [4] On the other hand, GO-VC has a high moisturizing power due to the binding of glycerin and can prevent the dryness of the skin.　In addition, GO-VC has a sterilizing activity of octanol, so it has a sterilizing activity against many bacteria.

GO-VC is also used for wound healing and wrinkle prevention because it has a proliferative effect on fibroblasts and a promoting effect on type I collagen production. GO-VC has a stronger melanin production inhibitory effect than arbutin, which is used as a whitening agent, and it was confirmed in clinical trials that even low concentrations of 0.01 to 0.1% (by weight) are effective against acne redness and pigmentation.

The water-soluble vitamin C derivatives such as ascorbic acid 2-glucoside and APPS (trisodium ascorbyl palmitate) can not add to water-soluble polymer gels commonly used in cosmetics such as carboxy vinyl polymer and sodium polyacrylate. This is because the viscosity changes, causing precipitation. On the other hand, GO-VC can be dispersed in water-soluble polymer gel transparently and uniformly or can be stably dissolved for a long time.

The fat-soluble vitamin C derivatives such as ascorbyl tetrahexyl decanoate (VC-IP) are almost insoluble in water, making it difficult to mix in water-soluble formulations such as lotions without the use of surfactants. Fat-soluble vitamin C derivatives causes lipid oxidation problems when lipids are released, and the color of the formulation tends to change.　GO-VC can solve these problems almost completely.

GO-VC is well absorbed percutaneously due to its amphiphilic nature, and because it is negatively charged rather than completely non-ionic, it can facilitate percutaneous absorption with an iontophoresis device. In addition, GO-VC is amphipathic but does not have a lipid group, so there are few skin toxicity problems due to lipid peroxidation, and it does not have the sticky feeling of conventional vitamin C derivatives and has a good feel. [5]

Stability

When the aqueous solution containing vitamin C and GO-VC was stored at 50 °C for 90 days, the vitamin C residual amount decreased to less than 30% in 30 days, whereas the residual amount of GO-VC was 90% or more. Moreover, after 90 days, 80% or more of GO-VC was confirmed to remain.

It is considered that these high stability are due to the two most reactive hydroxyl groups of vitamin C being capped by glycerin and octanol at the same time. Because the viscosity is stable in the preparation containing GO-VC and the polymer gel too, and it can be kept in a transparent state for a long period of time. Therefore, GO-VC can be added to many preparations such as lotions, creams, serums and gels. [6]

Acne

It was reported that GO-VC is effective against post-inflammatory hyperpigmentation (PIH), post-inflammatory erythema (PIE), and atrophic scar (AS), which are important complications in acne. It applied a complex vitamin C derivative lotion containing GO-VC to each of 10 patients with acne twice on the right side twice a day for 3 months, and confirmed the left side without application and its effect. It was reported that there was a marked improvement in PIH, PIE, and AS on the only right side applying lotion containing GO-VC after 3 months. [7] [8]

Pigmentation

Many phenolic compounds, which are conventional whitening agents, react with tyrosinase to induce melanocyte-specific cytotoxicity, and thus there was a risk of developing vitiligo. [9] GO-VC reduced the intracellular melanin content of B16 melanoma cells. GO-VC's pigmentation inhibitory mechanism is shown to act through a novel melanogenesis inhibitory system that does not depend on tyrosinase activity inhibition, indicating that it is a safe and effective pigmentation inhibitor with low risk of vitiligo. GO-VC showed a remarkable effect in an actual pigmentation suppression clinical study, and a gel preparation containing 0.1% GO-VC was applied twice a day in the morning and evening on the entire face after 13 female subjects aged 39.8 years on average. As a result of a 1-5 month study, GO-VC significantly improved post-inflammatory pigmentation. It is reported that GO-VC also showed a clear improvement in pigmentation caused by metal allergy, which was not very effective when applied with hydroquinone. [10]

Since conventional water-soluble vitamin C does not easily penetrate the skin barrier, an amphipathic vitamin C derivative was developed to improve this. However, since lipids such as palmitic acid were chemical modified to vitamin C derivatives in the past, exposure to ultraviolet light generated free fatty acids, raising concerns about lipid peroxidation. It was thought that GO-VC could avoid the problem of lipid peroxidation because GO-VC is amphipathic with octanol instead of lipid. The effect of 0.05% gel of GO-VC was investigated on skin pore related diseases. As a result, it was confirmed that there were no side effects and the number of abnormal pores decreased to 70% or less within 1 to 2 months after application. [11]

Related Research Articles

<span class="mw-page-title-main">Chemistry of ascorbic acid</span> Chemical compound

Ascorbic acid is an organic compound with formula C
6H
8O
6, originally called hexuronic acid. It is a white solid, but impure samples can appear yellowish. It dissolves freely in water to give mildly acidic solutions. It is a mild reducing agent.

<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, also sold as a dietary supplement and as a topical "serum" ingredient to treat melasma and wrinkles on the face. It is used to prevent and treat scurvy. Vitamin C is an essential nutrient involved in the repair of tissue, the formation of collagen, and the enzymatic production of certain neurotransmitters. It is required for the functioning of several enzymes and is important for immune system function. It also functions as an antioxidant. Most animals are able to synthesize their own vitamin C. However, apes and monkeys, most bats, most fish, some rodents, and certain other animals must acquire it from dietary sources because a gene for a synthesis enzyme has mutations.

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

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

<span class="mw-page-title-main">Triglyceride</span> Any ester of glycerol having all three hydroxyl groups esterified with fatty acids

A triglyceride is an ester derived from glycerol and three fatty acids. Triglycerides are the main constituents of body fat in humans and other vertebrates, as well as vegetable fat. They are also present in the blood to enable the bidirectional transference of adipose fat and blood glucose from the liver, and are a major component of human skin oils.

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

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

A humectant is a hygroscopic (water-absorbing) substance used to keep things moist. They are used in many products, including food, cosmetics, medicines and pesticides. When used as a food additive, a humectant has the effect of keeping moisture in the food. Humectants are sometimes used as a component of antistatic coatings for plastics.

<span class="mw-page-title-main">Hyperpigmentation</span> Darkening of an area of skin or nails caused by increased melanin

Hyperpigmentation is the darkening of an area of skin or nails caused by increased melanin.

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

Sebacic acid is a naturally occurring dicarboxylic acid with the chemical formula HO2C(CH2)8CO2H. It is a white flake or powdered solid. Sebaceus is Latin for tallow candle, sebum is Latin for tallow, and refers to its use in the manufacture of candles. Sebacic acid is a derivative of castor oil.

The term cleanser refers to a product that cleans or removes dirt or other substances. A cleanser could be a detergent, and there are many types of cleansers that are produced with a specific objective or focus. For instance, a degreaser or carburetor cleanser used in automotive mechanics for cleaning certain engine and car parts.

<span class="mw-page-title-main">Concealer</span> Type of cosmetic

A concealer or color corrector is a type of cosmetic that is used to mask imperfections on the skin. These imperfections can include dark circles under the eyes, blemishes, and hyperpigmentation. Concealer is similar to, and can be used in conjunction with foundation, a lighter cosmetic that is used to even out the skin tone. Both concealer and foundation are typically used to make skin appear more uniform in color. These two types of cosmetics differ in that concealers tend to be more heavily pigmented, though concealer and foundation are both available in a wide range of colors opacities.

<span class="mw-page-title-main">Azelaic acid</span> Organic chemical compound

Azelaic acid (AzA) is an organic compound with the formula HOOC(CH2)7COOH. This saturated dicarboxylic acid exists as a white powder. It is found in wheat, rye, and barley. It is a precursor to diverse industrial products including polymers and plasticizers, as well as being a component of a number of hair and skin conditioners. AzA inhibits tyrosinase.

<span class="mw-page-title-main">Carboxymethyl cellulose</span> Cellulose derivative grafted with carboxymethyl groups

Carboxymethyl cellulose (CMC) or cellulose gum is a cellulose derivative with carboxymethyl groups (-CH2-COOH) bound to some of the hydroxyl groups of the glucopyranose monomers that make up the cellulose backbone. It is often used as its sodium salt, sodium carboxymethyl cellulose. It used to be marketed under the name Tylose, a registered trademark of SE Tylose.

<span class="mw-page-title-main">Panthenol</span> Pair / mixture of stereoisomers

Panthenol (also called pantothenol) is the alcohol analog of pantothenic acid (vitamin B5), and is thus a provitamin of B5. In organisms, it is quickly oxidized to pantothenic acid. It is a viscous transparent liquid at room temperature. Panthenol is used in pharmaceutical and cosmetic products as a moisturizer and to improve wound healing.

Erythromycin/isotretinoin is a topical gel with two active ingredients: erythromycin 2% w/w and isotretinoin 0.05% w/w with a primary indication for the treatment of moderate acne vulgaris.

Rose hip seed oil is a pressed seed oil, extracted from the seeds of the wild rose bush Rosa rubiginosa in the southern Andes. Rosehip seed oil can also be extracted from Rosa canina, a wild rose species native to Europe, northwest Africa, and western Asia. The fruits of the rosehip have been used in folk medicine for a long time. Rosehips have prophylactic and therapeutic actions against the common cold, infectious diseases, gastrointestinal disorders, urinary tract diseases, and inflammatory diseases.

<span class="mw-page-title-main">2-Octanol</span> Chemical compound

2-Octanol is an organic compound with the chemical formula CH3CH(OH)(CH2)5CH3. It is a colorless oily liquid that is poorly soluble in water but soluble in most organic solvents. 2-Octanol is classified fatty alcohol. A secondary alcohol, it is chiral.

<span class="mw-page-title-main">Jagannath Ganguly</span>

Jagannath Ganguly (1921–2007) was an Indian biochemist known for his researches on Vitamin A and fatty acids, which assisted in the better understanding of their metabolism in humans. Born on the 1 April 1921, he authored a book, Biochemistry of Vitamin A, which details the physiological, biochemical and nutritional characteristics of the organic compound. The Council of Scientific and Industrial Research, the apex agency of the Government of India for scientific research, awarded him the Shanti Swarup Bhatnagar Prize for Science and Technology, one of the highest Indian science awards, in 1963, for his contributions to biological sciences. He died on 12 December 2007.

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

Ascorbyl glucoside (AA-2G) is an ascorbic acid derivative that contains at least one glycosyl group. Ascorbyl glucoside is commonly used in cosmetic products to administer vitamin C topically. Ascorbyl glucoside exhibits superior stability and penetration ability compared to ascorbyl phosphate salts, but the rate of its in vivo conversion to ascorbic acid is not known. Ascorbyl glucosides such as AA-2G, like many other derivatives of the ascorbic acid, show antiscorbutic effects. It is also sometimes used in skin whitening products.

References

  1. ↑ "カプリリル２－グリセリルアスコルビン酸—Caprylyl 2-Glyceryl Ascorbate". Japan Cosmetic Industry Association. Retrieved 2020-09-29.
  2. ↑ Ito, Shinobu (2018). "Whitening agents and their mechanism attracting attention in the field of aesthetic medicine". Fragrance Journal (Japanese). 4: 12–18.
  3. ↑ Ito, Shinobu; Itoga, Kazuyoshi; Yamato, Masayuki; Akamatsu, Hirohiko; Okano, Teruo (January 2010). "The co-application effects of fullerene and ascorbic acid on UV-B irradiated mouse skin". Toxicology. 267 (1–3): 27–38. doi:10.1016/j.tox.2009.09.015. PMID   19800932.
  4. ↑ Ito, Shinobu (2003). Provitamin C, Skin Care Course 20 (in Japanese). Tokyo: Gendai Shyorin. ISBN   4-7745-0524-2.
  5. ↑ Ito, Shinobu; Niki, Etsuo; Hata, Ryuichirou (May 2014). Provitamin C, The unknown function of vitamin C derivatives with molecular design (in Japanese). Tokyo: Fragrance journal. ISBN   978-4-89479-244-9.
  6. ↑ Nagata, Takeshi; et al. (2015). "Clinical effect of GO-VC, a new amphipathic vitamin C derivative (Japanese)". Fragrance Journal. 43 (9): 39–44.
  7. ↑ Kurokawa, Ichiro; Yoshioka, Masato; Ito, Shinobu (October 2019). "Split-face comparative clinical trial using glyceryl-octyl-ascorbic acid/ascorbyl 2-phosphate 6-palmitate/DL-α-tocopherol phosphate complex treatment for postinflammatory hyperpigmentation, postinflammatory erythema and atrophic scar in acne vulgaris". The Journal of Dermatology. 46 (10): e347–e348. doi:10.1111/1346-8138.14930. PMID   31149741. S2CID   171093399.
  8. ↑ Kurokawa, Ichiro (2015). "Effect of new vitamin C derivative on acne (Japanese)". Fragrance Journal. 9: 26–30.
  9. ↑ Nagata, Takeshi; Ito, Shinobu; Itoga, Kazuyoshi; Kanazawa, Hideko; Masaki, Hitoshi (2015). "The Mechanism of Melanocytes-Specific Cytotoxicity Induced by Phenol Compounds Having a Prooxidant Effect, relating to the Appearance of Leukoderma". BioMed Research International. 2015: 479798. doi: 10.1155/2015/479798 . PMC   4377363 . PMID   25861631. S2CID   10264822.
  10. ↑ Akira, Kawada; Satoko, Takase; Kaoru, Sato; Ayako, Mori; Chika, Okumura; Satsuki, Osame; Amiko, Sato; Shinobu, Ito (November 2019). Female dermatologist teaches, Supervitamin C facials, 6 female doctors explain how to use supervitamin C derivatives (Japanese). Tokyo: Nikkei BP. ISBN   978-4-296-10346-1.
  11. ↑ Ito, Shinobu (2017). "Effect of provitamin C on abnormal pores. (Japanese)". Fragrance Journal. 45 (2): 39–45.
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