Carapa guaianensis oil polyglyceryl-6 esters is an emulsifying agent derived from the esterification of polyglyceryl-6, a hydrophilic (water-attracting) compound, and the oil extracted from the seeds of the Carapa guaianensis tree, also known as andiroba. The combination of polyglyceryl-6 with andiroba oil produces a mild, skin-friendly ingredient used primarily in cosmetics and personal care products. It stabilizes emulsions, ensuring the smooth and even mixing of oil and water-based components. It is valued for its moisturizing and conditioning properties while benefiting from the bioactive properties of andiroba oil.
Chemical Composition and Structure
Carapa guaianensis oil polyglyceryl-6 esters is a complex compound formed through the esterification of polyglyceryl-6 and fatty acids from andiroba oil. The polyglyceryl-6 portion consists of a polymer of glycerol, providing water-binding properties, while the fatty acids from andiroba oil, rich in oleic, linoleic, and palmitic acids, offer hydrophobic characteristics. This combination makes it an excellent emulsifier, capable of stabilizing oil-in-water and water-in-oil emulsions, improving the texture and consistency of cosmetic formulations.
Physical Properties
Carapa guaianensis oil polyglyceryl-6 esters typically appears as a pale yellow to amber liquid or semi-solid. It is soluble in oils and dispersible in water, making it ideal for emulsification in various cosmetic and personal care products. Its melting point varies depending on its specific formulation, but it generally has a low viscosity, allowing it to be easily incorporated into formulations without affecting the overall texture or flow of the product. It contributes to a smooth, non-greasy feel in skincare formulations.
Production Process
The production of Carapa guaianensis oil polyglyceryl-6 esters involves several steps:
Extraction of Andiroba Oil: The oil is extracted from the seeds of the Carapa guaianensis tree, typically through mechanical pressing or solvent extraction, followed by refining to remove impurities.
Synthesis of Polyglyceryl-6: Polyglyceryl-6 is synthesized from glycerol through polymerization, creating a hydrophilic compound with multiple hydroxyl groups that enhance water-binding capacity.
Esterification: The andiroba oil is esterified with polyglyceryl-6 under controlled conditions to form the final ester compound, which combines the benefits of the oil's bioactive properties with the emulsifying capabilities of polyglyceryl-6.
Purification and Formulation: The esterified product is refined and purified before being incorporated into cosmetic formulations.
Applications
Cosmetics: Carapa guaianensis oil polyglyceryl-6 esters is primarily used as an emulsifier and conditioning agent in skin care products, such as creams, lotions, and serums. It enhances the spreadability and texture of these products while delivering the bioactive benefits of andiroba oil, such as anti-inflammatory and moisturizing properties. It helps maintain the stability of emulsions, preventing the separation of oil and water phases, and contributes to a smooth, non-greasy finish on the skin.
Hair Care: In hair care products, this ingredient acts as a conditioning agent, improving hair softness and manageability. It is used in shampoos, conditioners, and hair masks to promote scalp health and reduce dryness, thanks to the nourishing fatty acids from andiroba oil.
Sun Care and After-Sun Products: Carapa guaianensis oil polyglyceryl-6 esters is used in sun care formulations due to its ability to help distribute active ingredients evenly across the skin, enhancing the protective properties of sunscreens. It also provides soothing and moisturizing benefits, making it suitable for after-sun care products.
CAS: 352458-32-3 906347-26-0
Funzioni INCI:
Skin conditioning agent - Emollient. Emollients have the characteristic of enhancing the skin barrier through a source of exogenous lipids that adhere to the skin, improving barrier properties by filling gaps in intercorneocyte clusters to improve hydration while protecting against inflammation. In practice, they have the ability to create a barrier that prevents transepidermal water loss. Emollients are described as degreasing or refreshing additives that improve the lipid content of the upper layers of the skin by preventing degreasing and drying of the skin. The problem with emollients is that many have a strong lipophilic character and are identified as occlusive ingredients; they are oily and fatty materials that remain on the skin surface and reduce transepidermal water loss. In cosmetics, emollients and moisturisers are often considered synonymous with humectants and occlusives.
Environmental and Safety Considerations
Carapa guaianensis oil polyglyceryl-6 esters is generally regarded as safe for use in cosmetic and personal care formulations. It is non-irritating and non-sensitizing, making it suitable for sensitive skin. The ingredient is also biodegradable, minimizing its environmental impact when used in wash-off products.
However, as andiroba oil is derived from the Carapa guaianensis tree, it is crucial that the oil is sourced sustainably to prevent deforestation and ensure the preservation of biodiversity in the Amazon and other tropical regions. Sustainable sourcing practices not only protect the environment but also support local communities that rely on andiroba harvesting.
Applications of Carapa guianensis plant
- Medicinal: Carapa guianensis oil is applied topically to relieve skin irritation and inflammation (1), and orally to treat fever and parasites (2).
It was also found a hepatoprotective effect due to the limonoids present in the seeds and flowers of this plant (3).
- Cosmetic: Used in soaps, lotions, and creams for its moisturizing and skin-protective qualities.
INCI Functions:
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.
- Industrial: The wood is used in carpentry and construction due to its strong and resistant nature.
For more information:
Carapa guaianensis
References__________________________________________________________________________
(1) Henriques Md, Penido C. The therapeutic properties of Carapa guianensis. Curr Pharm Des. 2014;20(6):850-6. doi: 10.2174/13816128113199990048.
Abstract. Carapa guianensis Aublet (Meliaceae), also known as andiroba, is used in popular medicine in Brazil and other countries encompassing the Amazon rainforest. Virtually all parts of the andiroba tree are utilized, including the seed's oil, which is employed to treat inflammation and infections. The medicinal properties of C. guianensis have been attributed to the presence of limonoids, which are tetranortriterpenoids. We have previously demonstrated that the oil obtained from C. guianensis seeds contains different tetranortriterpenoids, including 6α-acetoxygedunin, 7-deacetoxy-7-oxogedunin, andirobin, gedunin and methyl-angolensate. The seeds oil and this fraction of tetranortriterpenoids present marked anti-inflammatory and anti-allergic properties, by inhibiting edema formation in different experimental models in rodents, via the impairment of signaling pathways triggered by histamine, bradykinin and platelet-activating factor. Tetranortriterpenoids also impaired the production of inflammatory mediators that trigger leukocyte infiltration into the inflammatory site, including the eosinophilotactic mediators interleukin (IL)-5 and CCL11/eotaxin, as well as the inflammatory cytokines tumor necrosis factor (TNF)-α and IL-1β. This phenomenon seems to depend on the inhibition of nuclear factor κB (NFκB) activation. We have further demonstrated that each one of the five tetranortriterpenoids listed above presented inhibitory effects on the activation of different cell populations, including mast cells, eosinophils and T lymphocytes, through which they impaired allergy and inflammation. This review will discuss the therapeutic effects of C. guianensis oil and its compounds, focusing on the scientific evidences that support its traditional use in inflammatory conditions and its anti-allergic properties.
Araujo-Lima CF, Fernandes AS, Gomes EM, Oliveira LL, Macedo AF, Antoniassi R, Wilhelm AE, Aiub CAF, Felzenszwalb I. Antioxidant Activity and Genotoxic Assessment of Crabwood (Andiroba, Carapa guianensis Aublet) Seed Oils. Oxid Med Cell Longev. 2018 May 2;2018:3246719. doi: 10.1155/2018/3246719.
Abstract. The seed oil of Carapa guianensis (Aublet), a tree from the Meliaceae family commonly known as andiroba, is widely used in Brazilian traditional medicine because of its multiple curative properties against fever and rheumatism and as an anti-inflammatory agent, antibacterial agent, and insect repellant. Since there is no consensus on the best way to obtain the C. guianensis oil and due to its ethnomedicinal properties, the aim of the present research was to evaluate the chemical composition, free-radical scavenging activity, and mutagenic and genotoxicity properties of three C. guianensis oils obtained by different extraction methods. The phenolic contents were evaluated by spectrophotometry. Oil 1 was obtained by pressing the dried seeds at room temperature; oil 2 was obtained by autoclaving, drying, and pressing; oil 3 was obtained by Soxhlet extraction at 30-60°C using petroleum ether. The oil from each process presented differential yields, physicochemical properties, and phenolic contents. Oil 1 showed a higher scavenging activity against the DPPH radical when compared to oils 2 and 3, suggesting a significant antioxidant activity. All oils were shown to be cytotoxic to bacteria and to CHO-K1 and RAW264.7 cells. At noncytotoxic concentrations, oil 2 presented mutagenicity to Salmonella enterica serovar Typhimurium and induced micronuclei in both cell types. Under the same conditions, oil 3 also induced micronucleus formation. However, the present data demonstrated that oil 1, extracted without using high temperatures, was the safest for use as compared to the other two oils, not showing mutagenicity or micronucleus induction.
(2) Oliveira IDSDS, Moragas Tellis CJ, Chagas MDSDS, Behrens MD, Calabrese KDS, Abreu-Silva AL, Almeida-Souza F. Carapa guianensis Aublet (Andiroba) Seed Oil: Chemical Composition and Antileishmanial Activity of Limonoid-Rich Fractions. Biomed Res Int. 2018 Sep 6;2018:5032816. doi: 10.1155/2018/5032816.
Abstract. Leishmaniasis is a complex of diseases caused by protozoa of the genus Leishmania and affects millions of people around the world. Several species of plants are used by traditional communities for the treatment of this disease, among which is Carapa guianensis Aubl. (Meliaceae), popularly known as andiroba. The objective of the present work was to conduct a chemical study of C. guianensis seed oil and its limonoid-rich fractions, with the aim of identifying its secondary metabolites, particularly the limonoids, in addition to investigating its anti-Leishmania potential. The chemical analyses of the C. guianensis seed oil and fractions were obtained by electrospray ionization mass spectrometry (ESI-MS). The cytotoxic activity was tested against peritoneal macrophages, and antileishmanial activity was evaluated against promastigotes and intracellular amastigotes of Leishmania amazonensis. All the C. guianensis seed oil samples analyzed exhibited the same pattern of fatty acids, while the limonoids 7-deacetoxy-7-hydroxygedunin, deacetyldihydrogedunin, deoxygedunin, andirobin, gedunin, 11β-hydroxygedunin, 17-glycolyldeoxygedunin, 6α-acetoxygedunin, and 6α,11β-diacetoxygedunin were identified in the limonoid-rich fractions of the oil. The C. guianensis seed oil did not exhibit antileishmanial activity, and cytotoxicity was higher than 1000 μg/mL. Three limonoid-rich oil fractions demonstrated activity against promastigotes (IC50 of 10.53±0.050, 25.3±0.057, and 56.9±0.043μg/mL) and intracellular amastigotes (IC50 of 27.31±0.091, 78.42±0.086, and 352.2±0.145 μg/mL) of L. amazonensis, as well as cytotoxicity against peritoneal macrophages (CC50 of 78.55±1.406, 139.0±1.523, and 607.7±1.217 μg/mL). The anti-Leishmania activity of the limonoid-rich fractions of C. guianensis can be attributed to the limonoids 11β-hydroxygedunin and 6α,11β-diacetoxygedunin detected in the chemical analysis.
(3) Ninomiya K, Miyazawa S, Ozeki K, Matsuo N, Muraoka O, Kikuchi T, Yamada T, Tanaka R, Morikawa T. Hepatoprotective Limonoids from Andiroba (Carapa guianensis). Int J Mol Sci. 2016 Apr 19;17(4):591. doi: 10.3390/ijms17040591.
Abstract. Three gedunin-type limonoids, gedunin (1), 6α-acetoxygedunin (2), and 7-deacetoxy-7-oxogedunin (3), which were isolated from the seed and flower oils of andiroba (Carapa guianensis Aublet, Meliaceae), exhibited hepatoprotective effects at doses of 25 mg/kg, p.o. against d-galactosamine (d-GalN)/lipopolysaccharide (LPS)-induced liver injury in mice. To characterize the mechanisms of action of 1-3 and clarify the structural requirements for their hepatoprotective effects, 17 related limonoids (1-17) isolated from the seed and/or flower oils of C. guianensis were examined in in vitro studies assessing their effects on (i) d-GalN-induced cytotoxicity in primary cultured mouse hepatocytes, (ii) LPS-induced nitric oxide (NO) production in mouse peritoneal macrophages, and (iii) tumor necrosis factor-α (TNF-α)-induced cytotoxicity in L929 cells. The mechanisms of action of 1-3 are likely to involve the inhibition of LPS-induced macrophage activation and reduced sensitivity of hepatocytes to TNF-α; however, these compounds did not decrease the cytotoxicity caused by d-GalN. In addition, the structural requirements of limonoids (1-17) for inhibition of LPS-induced NO production in mouse peritoneal macrophages and TNF-α-induced cytotoxicity in L929 cells were evaluated.
