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| 1g |
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| Other Sizes |
| Targets |
Stearoyl glutamic acid sodium does not have a specific biological target in the context of a drug or therapeutic agent. Rather, its mechanism of action in cosmetic formulations is physicochemical: it acts as an anionic surfactant and emulsifier. At oil-water interfaces, the molecule orients itself such that the hydrophobic stearoyl tail embeds in the oil phase, while the hydrophilic glutamic acid head group (which carries a net negative charge at neutral pH) interacts with the aqueous phase. This arrangement lowers the interfacial tension, allowing the formation of stable oil-in-water (O/W) emulsions used in creams and lotions. In terms of biosafety, the compound is also recognized as an amino acid alkyl amide sensitizer, meaning that it can bind to proteins in the skin and elicit an allergic immune response in sensitized individuals, leading to allergic contact dermatitis (ACD). This sensitization potential is mediated by the hapten mechanism, where the chemical modifies self-proteins to become immunogenic.
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| ln Vitro |
In vitro studies of Stearoyl glutamic acid sodium have primarily focused on its physicochemical properties and its potential to cause skin sensitization rather than any therapeutic activity. The compound has been characterized in the context of self-emulsifying drug delivery systems (SEDDS), where its ability to form stable hydrophobic ion pairs with other compounds can influence drug release profiles. In cell culture, the compound is not typically used to assess biological activity but rather to evaluate its toxicity or sensitization potential. For instance, the Local Lymph Node Assay (LLNA) in vitro or the KeratinoSens assay (which measures activation of the antioxidant response element (ARE) in a keratinocyte cell line) can be used to predict skin sensitization hazard. Additionally, the compound has been used as an emulsifier in topical compounded preparations, where its effect on skin bioengineering parameters (e.g., transepidermal water loss, hydration) may be evaluated. No significant pro-inflammatory or cytotoxic activity has been reported beyond its surfactant properties at high concentrations.
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| ln Vivo |
No in vivo therapeutic activity has been reported for Stearoyl glutamic acid sodium, as it is not a drug. However, its potential to cause allergic contact dermatitis has been documented in humans. Case reports have identified cosmetics containing sodium stearoyl glutamate as a cause of allergic contact dermatitis on the face and other areas. In animal models, skin sensitization can be evaluated using the murine Local Lymph Node Assay (LLNA), where the compound is applied topically to the ears of mice (e.g., CBA/Ca mice) for three consecutive days. On day five, mice are injected with tritiated thymidine or BrdU, and lymph node cell proliferation is measured. A stimulation index (SI) ≥3 indicates a sensitizer. In guinea pig maximization tests, repeated topical application followed by challenge can be used to assess the compound's ability to induce delayed-type hypersensitivity. These studies have confirmed that sodium stearoyl glutamate can act as an amino acid alkyl amide sensitizer.
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| Enzyme Assay |
There is no established protocol for enzyme or receptor binding assays for Stearoyl glutamic acid sodium, as it does not have a specific biological target. However, for researchers interested in studying its interaction with serum albumin (a model carrier protein) or skin proteins (to understand haptenation), a standard fluorescence quenching or surface plasmon resonance (SPR) assay could be employed. A generic protocol: (1) Prepare solutions of human serum albumin (HSA) in phosphate-buffered saline (PBS, pH 7.4) at a fixed concentration (e.g., 5 uM). (2) Titrate increasing concentrations of Stearoyl glutamic acid sodium (0 to 100 uM) into the protein solution. (3) Measure the intrinsic fluorescence of tryptophan residues (excitation at 295 nm, emission at 340 nm) before and after each addition. (4) Analyze the data using the Stern-Volmer equation to calculate the binding constant. Alternatively, for haptenation studies, the compound can be incubated with a model protein (e.g., lysine-rich protein) and analyzed by mass spectrometry for the addition of the stearoyl group to lysine residues, forming covalent amide bonds.
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| Cell Assay |
Cellular assays for Stearoyl glutamic acid sodium are generally focused on assessing safety (cytotoxicity and sensitization) rather than activity. A standard protocol for assessing skin sensitization potential using the KeratinoSens assay (OECD TG 442D) involves culturing an immortalized keratinocyte cell line (HaCaT) that has been stably transfected with a luciferase gene under the control of an antioxidant response element (ARE). Cells are seeded in 96-well plates and allowed to attach overnight. The following day, the culture medium is replaced with medium containing varying, non-cytotoxic concentrations of the test compound (0.1-1000 ug/mL) or a positive control (e.g., 2,4-dinitrochlorobenzene, DNCB). After 48 hours of incubation, cell lysates are assayed for luciferase activity using a luminometer. A two-fold or greater induction of luciferase activity relative to vehicle-treated controls is considered a positive result for skin sensitization potential. Additionally, the MTT assay can be performed in parallel on separate plates to assess cell viability at the same concentrations.
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| Animal Protocol |
In vivo animal experiments for Stearoyl glutamic acid sodium are focused on its toxicological evaluation as a cosmetic ingredient rather than its efficacy. A standard protocol for a skin sensitization test in guinea pigs (Buehler test or Guinea Pig Maximization Test, GPMT) is often employed. In the GPMT, Hartley guinea pigs are first injected intradermally with an emulsion of the test compound (in Freund's complete adjuvant) to induce systemic immunity. After a rest period, the test compound is applied topically to the same animals to "challenge" the immune system. Skin reactions (erythema and edema) are scored at 24 and 48 hours after the challenge. An increased reaction compared to control animals indicates that the compound has potential to cause skin sensitization. Additionally, acute dermal toxicity studies (OECD TG 402) can be performed where the compound is applied to the shaved skin of rats under an occlusive dressing for 24 hours, followed by observation for 14 days to assess mortality and clinical signs. Stearoyl glutamic acid sodium is generally considered to have low acute dermal toxicity.
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| ADME/Pharmacokinetics |
Stearoyl glutamic acid sodium is not a drug and is not subject to systematic ADME (absorption, distribution, metabolism, excretion) studies in the context of pharmacology. However, as an ingredient in topical cosmetics, its dermal absorption is of interest. It is generally considered to have very low systemic absorption through intact skin due to its high molecular weight (435.6) and amphiphilic nature. If absorbed, the compound may be metabolized by hydrolysis (enzymatic cleavage of the amide bond) to yield stearic acid and glutamic acid, both of which are endogenous compounds. Stearic acid is a common dietary fatty acid that undergoes beta-oxidation, while glutamic acid enters the amino acid pool. Any intact compound would likely be excreted in urine and feces. The compound appears as a white to off-white powder and is stable at room temperature. It is poorly soluble in water, but can be dispersed as an emulsion. For stock preparation, it is soluble in DMSO at 5 mg/mL (11.48 mM) with ultrasonic assistance. Storage should be at 4degC in sealed containers, protected from moisture and light.
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| Toxicity/Toxicokinetics |
Toxicity Summary
The expert panel concluded that the following 115 amino acid alkylamides are safe under current cosmetic application methods and concentrations, provided that the formulation ensures they do not irritate the skin… Sodium stearoyl glutamate… Under certain conditions, they can be safely used in cosmetics. Stearoyl glutamic acid sodium (CAS 38517-23-6) has a low order of acute toxicity when applied to the skin; however, it is classified as a weak to moderate skin sensitizer. In clinical dermatology, it has been identified as an emerging cause of allergic contact dermatitis (ACD), particularly from cosmetic products like facial creams, sunscreens, and shampoos. Patch testing in patients with suspected cosmetic allergy often reveals positive reactions to sodium stearoyl glutamate at concentrations of 1-5% in petrolatum. While the sensitization rate is low relative to the widespread use of the ingredient, it is nonetheless recognized as a significant allergen in the category of "amino acid alkyl amides". No carcinogenicity, reproductive toxicity, or genotoxicity data are publicly available. The compound is considered safe for use in cosmetics when formulated to be non-sensitizing and is approved for use in many jurisdictions, including the EU and the US. |
| References |
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| Additional Infomation |
Sodium Stearoyl Glutamate is safe, provided the formulation ensures it does not irritate the skin... Sodium Stearoyl Glutamate...
Stearoyl glutamic acid sodium is widely used as a cosmetic ingredient due to its mildness compared to traditional anionic surfactants like sodium lauryl sulfate (SLS). Because it is derived from natural sources (stearic acid from vegetable oils and glutamic acid from fermented corn), it is often marketed as a "natural" or "green" emulsifier. In the International Nomenclature of Cosmetic Ingredients (INCI), it is listed as Sodium Stearoyl Glutamate. It is commonly found in products such as facial cleansers, body washes, sunscreens, and make-up removers. The compound functions as a primary emulsifier and co-emulsifier, often used in combination with fatty alcohols to create stable, elegant emulsions. In addition to its emulsifying properties, it provides a soft, creamy foam and leaves a pleasant after-feel on the skin. It is not a drug and has no clinical trial history or regulatory approval status as a therapeutic agent, nor is it intended for human ingestion. |
| Molecular Formula |
C23H42NNAO5
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|---|---|
| Molecular Weight |
435.57
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| Exact Mass |
435.296
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| CAS # |
38517-23-6
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| PubChem CID |
23688969
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| Appearance |
Solid Powder
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| Boiling Point |
600.3ºC at 760mmHg
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| Flash Point |
316.8ºC
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| LogP |
5.06
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
21
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| Heavy Atom Count |
30
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| Complexity |
445
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| Defined Atom Stereocenter Count |
1
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| SMILES |
[Na+].CCCCCCCCCCCCCCCCCC(N[C@H](C(=O)O)CCC([O-])=O)=O
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| InChi Key |
QKHBMQWPOUUMQZ-BDQAORGHSA-M
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| InChi Code |
InChI=1S/C23H43NO5.Na/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-21(25)24-20(23(28)29)18-19-22(26)27;/h20H,2-19H2,1H3,(H,24,25)(H,26,27)(H,28,29);/q;+1/p-1/t20-;/m0./s1
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| Chemical Name |
sodium (4S)-5-hydroxy-4-(octadecanoylamino)-5-oxopentanoate
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| Synonyms |
Sodium stearoyl glutamate
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: (1). Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~5 mg/mL (~11.48 mM; with ultrasonication)
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.2958 mL | 11.4792 mL | 22.9584 mL | |
| 5 mM | 0.4592 mL | 2.2958 mL | 4.5917 mL | |
| 10 mM | 0.2296 mL | 1.1479 mL | 2.2958 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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