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Coco-Glucoside
"Descrizione"
by Ark90 (12417 pt)
2024-Oct-13 19:50

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Coco-Glucoside is a non-ionic surfactant derived from coconut and sugar (glucose). It is primarily used in skin and hair care products as a gentle cleansing and foaming agent. Due to its natural origin and mildness on the skin, Coco-Glucoside is widely used in eco-friendly formulations and products for sensitive skin. It is biodegradable, non-irritating, and well-tolerated by the skin.

Chemical Composition and Structure
Coco-Glucoside is formed by combining a fatty alcohol derived from coconut oil (typically long-chain alcohols like lauryl) with glucose. This gives it an amphiphilic structure, with a hydrophilic (water-soluble) part and a lipophilic (oil-soluble) part, making it effective as a surfactant to remove impurities and oils from the skin and hair without causing irritation.

Breakdown of the name and function of the components

  • Coco - Refers to derivatives of coconut oil.
  • Glucoside - It's a glycoside, a molecule consisting of a sugar (in this case glucose) attached to a non-sugar component.

Description and function of the raw materials used in production

  • Coconut oil - Provides the fatty acids which, once saponified, can react with glucose.
  • Glucose - A simple sugar that serves as the sugary component in the glycoside.

Production Process

Coco-Glucoside is obtained through a condensation process between glucose, sourced from plants like corn, and fatty alcohols derived from coconut oil. This production method is considered sustainable, resulting in an eco-friendly and biodegradable surfactant. 

  • Preparation of Components: The main ingredients for producing Coco-Glucoside include glucose, obtained from vegetable starches (such as corn or potatoes), and coconut oils or fats. These components are weighed and prepared for the reaction.

  • Condensation Reaction: Glucose is mixed with fatty acids derived from coconut oil in a chemical reactor. The condensation reaction occurs in the presence of an acid catalyst and at controlled temperatures, promoting the formation of Coco-Glucoside.

  • Neutralization: After the condensation reaction, the mixture may be neutralized if necessary to ensure that the final product has a balanced pH.

  • Purification: The produced Coco-Glucoside is purified to remove any impurities and chemical residues. This may include filtration and washing processes to ensure a high-quality product.

  • Quality Control and Packaging: Finally, Coco-Glucoside undergoes quality control checks to verify its purity and functional properties. After analysis, it is packaged for distribution and use in cosmetic and skincare products.

In general, the synthesis of alkyl glucosides, such as coco-glucoside, involves the condensation of a sugar such as glucose with a fatty alcohol such as coconut alcohol. This reaction is typically catalysed by an enzyme, such as a glucosidase, that helps form the glycosidic bond between the sugar and the alcohol. The reaction can take place in a suitable solvent and the product can be purified by various methods, such as distillation or chromatography.

Note that this is a general description of the process, and specific conditions such as temperature, pressure, pH, enzyme concentration, etc. may vary depending on the exact method used. 

Physical Properties

Coco-Glucoside appears as a viscous liquid, clear to pale yellow in color, and is soluble in water. It is mild and produces a soft, creamy lather, making it ideal for gentle cleansing products. Thanks to its non-irritating nature, it is used in formulations for all skin and hair types, including sensitive ones. 

Applications

  • Facial and Body Cleansers: Used in gentle skin cleansers, liquid soaps, and body washes due to its mild foaming and cleansing properties, which do not strip the skin's natural oils.

  • Shampoos and Conditioners: Employed in shampoos and conditioners for its ability to cleanse the scalp and hair effectively without removing natural oils, leaving hair soft and well-conditioned.

  • Baby Care Products: Frequently found in products for baby skin care due to its gentle nature.

  • Natural and Organic Cosmetics: Popular in natural and organic cosmetics due to its natural origin and biodegradability.

Cosmetics

It is a non-ionic surfactant (removes dirt particles) and  it is used as a foaming agent and emulsifier, face masks, cleansing milk, baby soaps.

Cleansing agent. Ingredient that cleanses skin without exploiting the surface-active properties that produce a lowering of the surface tension of the stratum corneum. 

Foaming.  Its function is to introduce gas bubbles into the water for a purely aesthetic factor, which does not affect the cleaning process, but only satisfies the commercial aspect of the detergent by helping to spread the detergent. This helps in the commercial success of a cleansing formulation. Since sebum has an inhibiting action on the bubble, more foam is produced in the second shampoo.

Surfactant - Cleansing agent. Cosmetic products used to cleanse the skin utilise the surface-active action that produces a lowering of the surface tension of the stratum corneum, facilitating the removal of dirt and impurities. 

Cleanses the hair and increases combability. In the Duhring test it emerges as the least irritating of all surfactants.

CAS   110615-47-9 

Medical

Used in acne treatment.

Health and Safety Considerations

Safety in Use
Coco-Glucoside is generally considered safe for use in cosmetic and personal care products. It is not known to cause skin or eye irritation, making it suitable for sensitive skin. It is often used in formulations designed for easily irritated skin.

Allergic Reactions
Allergic reactions to Coco-Glucoside are extremely rare, as it is a mild surfactant. However, as with any cosmetic ingredient, it is always recommended to patch test the product on a small area of skin before use, especially if you have very sensitive skin.

Toxicity and Carcinogenicity
 It is considered safe by international regulatory authorities for cosmetic use.

Environmental Considerations
Coco-Glucoside is fully biodegradable and considered eco-friendly. It is produced from renewable resources, primarily coconut oil and sugar, and its production process has a minimal environmental impact. It is a popular choice in eco-friendly and natural cosmetics.

Regulatory Status
Coco-Glucoside is approved for use in cosmetics by major regulatory authorities, including the European Union and the Food and Drug Administration (FDA) in the United States.


The most relevant studies on the subject have been selected with a summary of their contents:

Coco-Glucoside studies

__________________________________________________________________________________

Formula and characteristics are similar to  Decyl glucoside. The most substantial differences are viscosity and pH


ViscositypH
Coco-Glucoside2500-6000 (mPa•s, 20℃)7.0-10.0
Decyl Glucoside1000-2500 (mPa•s, 20℃)11.5-12.5


_________________________________

Decyl glucoside (Caprylyl/capryl glucoside) is a chemical compound, derived from plants, usually palm trees. It occurs as a straw-yellow liquid with good solubility in water.


What it is used for and where it is used

Non-ionic, stabilising, PEG-free alkyl polyglucoside surfactant, designed for nanoparticle stabilisation (1). Stable foaming agent, rapidly biodegradable, low toxicity, low viscosity, low level of sodium salts. Has good alkali tolerance and electrolyte tolerance.

Used in cosmetics in liquid soaps and shampoos as a second surfactant with excellent caustic stability and solubility in highly concentrated salt, alkaline and surfactant solutions. Generally magnesium oxide and magnesium are present in amounts ranging from 100 ppm to 400 ppm.

Other uses:

  • chemical industry
  • oil extraction industry 
  • pesticide industry

Safety

The oestrogenicity of decyl glucoside was confirmed as a non-endocrine disrupting surfactant by its preparation method using zeolite catalysts. Its oestrogenicity was estimated using the E-assay method. Decyl glucoside was synthesized by direct glucosidation from D-glucose with 1-decanol. The conversion and yield were improved by increasing the amount of acid sites of the zeolite catalysts. Decyl glucopyranoside is more hydrophilic than nonylphenol and has a high wettability. Decyl glucopyranosides exhibited extremely lower proliferation of oestrogenic cells than nonylphenol. (2).

The Expert Group on Cosmetic Ingredient Control (CIR) evaluated the safety of 19 alkyl glucosides as used in cosmetics and concluded that these ingredients are safe in current use practices and concentrations when formulated to be non-irritating. Most of these ingredients function as surfactants in cosmetics, but some have additional functions such as skin conditioning agents, hair conditioning agents or emulsion stabilisers. The Panel reviewed the available animal and clinical data on these ingredients. As glucoside hydrolases in human skin are able to break down these ingredients to release their respective fatty acids and glucose, the Panel also reviewed CIR reports on the safety of fatty alcohols and were able to extrapolate from previous data to support their safety (3).

Decyl Glucoside studies

Typical optimal commercial product characteristics Caprylyl/Capryl Glucoside

AppearancePale yellow liquid
Viscosity1000-2500 (mPa•s, 20℃)
Density (g/cm3), 25°C1.07-1.09
Boiling Point
476.5±45.0 °C at 760 mmHg
Flash Point
242.0±28.7 °C


C chain distribution

C6

C8

C10

(base substance: Fatty alcohol)

0%~1%

53%~63%

33%~43%

PSA99.38000
LogP
pH11.5-12.5
Free Alcohol (wt %)
≤1.0
Vapour Pressure
0.0±2.7 mmHg at 25°C
Index of Refraction
1.512
Viscosity (mPa·s), 20°C
300-400  (at 20°C)

Specific Gravity at 25°C [g/cm3]

1.08-1.12
Water (wt %)
47-50
DP1.3-1.5
Surface tension (mN/m), 25°C, 0.1%
28-30
Microorganism (CFU/g)
≤10
Ash(wt%)
≤3.0



  • Molecular Formula C16H32O6
  • Molecular Weight 320.22 g/mol
  • Exact Mass   320.219879
  • CAS :   68515-73-1  141464-42-8   54549-25-6
  • UNII 
  • EC Number   500-220-1
  • DSSTox Substance ID    DTXSID70872594
  • MDL number  
  • PubChem Substance ID 
  • IUPAC  (3R,4S,5S,6R)-2-decoxy-6-(hydroxymethyl)oxane-3,4,5-trio
  • InChI=1S/C16H32O6/c1-2-3-4-5-6-7-8-9-10-21-16-15(20)14(19)13(18)12(11-17)22-16/h12-20H,2-11H2,1H3/t12-,13-,14+,15-,16?/m1/s1 
  • InChl Key      JDRSMPFHFNXQRB-IWQYDBTJSA-N
  • SMILES    CCCCCCCCCCOC1C(C(C(C(O1)CO)O)O)O
  • SCHEMBL   43196

Synonyms :

  • Caprylyl/Capryl Glucoside
  • Alkyl Polyglycoside
  • APG
  • Glucoside, decyl
  • Decyl D-glucoside
  • Decyl D-glucopyranoside
  • Capryl glycoside
  • decyl-d-glucoside
  • (3R,4S,5S,6R)-2-decoxy-6-(hydroxymethyl)oxane-3,4,5-triol
  • (3R,4S,5S,6R)-2-(Decyloxy)-6-(hydroxymethyl)-tetrahydro-2H-Pyran-3,4,5-triol

References______________________________

(1) Kovačević AB, Müller RH, Keck CM. Formulation development of lipid nanoparticles: Improved lipid screening and development of tacrolimus loaded nanostructured lipid carriers (NLC). Int J Pharm. 2020 Feb 25;576:118918. doi: 10.1016/j.ijpharm.2019.118918.

(2) Chung KH, Kim H, Park YK, Kim BH, Kim SJ, Jung SC. Decyl Glucoside Synthesized by Direct Glucosidation of D-Glucose Over Zeolite Catalysts and Its Estrogenicity as Non-Endocrine Disruptive Surfactant. J Nanosci Nanotechnol. 2019 Feb 1;19(2):1172-1175. doi: 10.1166/jnn.2019.15900. 

(3) Fiume MM, Heldreth B, Bergfeld WF, Belsito DV, Hill RA, Klaassen CD, Liebler D, Marks JG Jr, Shank RC, Slaga TJ, Snyder PW, Andersen FA. Safety assessment of decyl glucoside and other alkyl glucosides as used in cosmetics. Int J Toxicol. 2013 Sep-Oct;32(5 Suppl):22S-48S. doi: 10.1177/1091581813497764.

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