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Xylitylglucoside
"Descrizione"
by Ark90 (12417 pt)
2023-Dec-05 12:44

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Xylitylglucoside is a chemical, carbohydrate-derived compound, industrially produced by fermentation of grain, wood or plant sugars. In particular, xylitol and glucose are used.

The name describes the structure of the molecule

  • "Xylityl" is derived from "xylitol", an alditol (a type of sugar alcohol) found in many plants and used as a sweetener.
  • "Glucoside" refers to a glycoside derived from glucose. Glycosides are compounds formed from the reaction between a sugar and another non-sugar molecule.

Description of raw materials used in production

  • Xylitol - A sugar alcohol obtained from birch bark and other wood sources.
  • Glucoside - A glycoside obtained from glucose.

Step-by-step summary of industrial chemical synthesis process

  • Extraction - Xylitol is extracted from natural sources like birch bark.
  • Reaction - Xylitol reacts with glucoside in the presence of a catalyst and under controlled temperature and pressure conditions.
  • Purification - The reacted mixture is purified to remove impurities and get pure xylitylglucoside.
  • Crystallization - The purified solution is cooled to form xylitylglucoside crystals.
  • Filtration - The crystals are separated from the solution through filtration.
  • Drying - The crystals are then dried to remove residual moisture.

It is presented in a light yellow liquid form.

What it is used for and where

Cosmetics

It is included in creams and personal care products as a humectant and moisturising agent that maintains the water content of a cosmetic both in the packaging and on the skin.

Humectant. Hygroscopic compound used to minimise water loss in the skin and to prevent it from drying out by facilitating faster and greater absorption of water into the stratum corneum of the epidermis.  The epidermis is the most superficial of the three layers that make up human skin (epidermis, dermis and hypodermis) and is the layer that maintains hydration in all three layers. In turn, the epidermis is composed of five layers: horny, the most superficial, granular, spinous, shiny, and basal. Humectants have the ability to retain the water they attract from the air in the stratum corneum and have the function of moisturising the skin. They are best used before emollients, which are oil-based.

Skin conditioning agent. It is the mainstay of topical skin treatment as it has the function of restoring, increasing or improving skin tolerance to external factors, including melanocyte tolerance. The most important function of the conditioning agent is to prevent skin dehydration, but the subject is rather complex and involves emollients and humectants that can be added in the formulation.

Usage: 1%-3%.

Datasheet   STD1422 Public Report.docx (industrialchemicals.gov.au) 

Commercial Applications

Cosmetics and Skincare. Used as a moisturizing agent to enhance the skin's ability to retain water, thereby improving its hydration.

Anti-aging Products. As it can boost skin moisture and elasticity, it's often included in products aiming to reduce wrinkles and other signs of aging.

Hair Care Products. Can be used in conditioners and hair masks to increase moisture and improve hair texture.

Studies

Xylitylglucoside is effective as a moisturizing agent and on skin barrier function to an extent at least equal to glycerin (1).

Typical commercial product characteristics  Xylitylglucoside

AppearanceLiquid
Boiling Point315°C at 101.3 kPa
Flash Point244°C at 101.3 kPa
Density1435 kg/m3 at 20°C
Melting Point<50°C
Vapour Pressure3.6 x 10-7 kPa at 25°C
Water Solubility674 g/L at 20°C
Autoignition> 423°C 



  • Molecular Formula  C11H22O10
  • Molecular Weight     314.29
  • Exact Mass   314.12100
  • CAS  1095751-96-4
  • UNII    O0IEZ166FB
  • EC Number   
  • DSSTox Substance ID  
  • IUPAC  (2S,3R,4R)-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypentane-1,2,3,4-tetrol
  • InChI=1S/C11H22O10/c12-1-4(14)7(16)5(15)3-20-11-10(19)9(18)8(17)6(2-13)21-11/h4-19H,1-3H2/t4-,5+,6+,7+,8+,9-,10+,11+/m0/s1 
  • InChl Key      LTBAFRQKFIMYQK-DLWPFLMGSA-N
  • SMILES   C(C1C(C(C(C(O1)OCC(C(C(CO)O)O)O)O)O)O)O
  • MDL number  
  • PubChem Substance ID    
  • RXCUI     1314249

Synonyms:

  • D-Xylitol, 5-O-beta-D-glucopyranosyl-
  • (2S,3R,4R)-5-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypentane-1,2,3,4-tetrol

References________________________________________________________________________

(1) Garcia, C., Valin, E., Hernandez, E., Kern, C., & Roso, A. (2023). Effect of a Simple Sugar-based Ingredient on Skin Moisturization: Biological Mode of Action and Clinical Effects. Asian Journal of Beauty and Cosmetology, 21(1), 13-27.

Abstract. Purpose: The study aimed to investigate the effects of a sugar-based structure, i.e. XAX (Xylitylglucoside-Anhydroxylitol-Xylitol) on skin barrier function and moisturization, both in vitro and in vivo, and to compare its efficacy with that of glycerin. Methods: Expression of genes was investigated by RT-qPCR analysis on topically-treated human reconstructed epidermis. Ceramide neosynthesis was measured by chromatography in topically-treated human skin explants. Production of essential proteins was monitored in primary cell cultures: Chondroitin sulfate and hyaluronic acid in fibroblasts, using chromatography; hyaluronic acid in keratinocytes, using ELISA. In vivo, epidermal microrelief, skin capacitance and transepidermal water loss (TEWL) were measured on 25 female volunteers with dry skin. Skin capacitance and TEWL were also measured, on hands, comparing hydroalcoholic gels. Results: XAX increased the expression of key moisturizing-related genes, such as enzymes, structural components or regulators of inter-keratinocytes junctions, cornified layer, desquamation process, as well as skin barrier function and hydration. It also increased the contents of ceramides, hyaluronic acid and chondroitin sulfate. In vivo, XAX treatment at 3% decreased TEWL and increased skin capacitance, skin microrelief and desquamation. The combination of XAX+glycerin (1.5%+1.5%) showed interesting effects compared to glycerin alone. Conclusion: XAX promoted effects on the biological pathways involved in skin barrier function; epidermal and dermal water reserves; and epidermal water circulation. Its effectiveness, confirmed in vivo, alone and in combination with glycerin, makes it an interesting alternative to basic emollients, humectants and occlusives.

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