Product Introduction
D-pyroglutamic acid, also known as D-PCA, is a derivative of glutamic acid [1]. It is a chiral molecule, existing in both L and D forms, but the D form is less common in nature [2]. This amino acid derivative is known for its role as a hygroscopic agent in cosmetics and its potential applications in pharmaceuticals [3]. It is also involved in various biochemical pathways [4].
Production Process
The production of D-pyroglutamic acid typically involves chemical synthesis processes [5]. One method includes the cyclization of D-glutamic acid under specific conditions [6]. This process involves heating D-glutamic acid in acidic or basic conditions to induce intramolecular dehydration, forming a lactam ring [7]. The resulting D-pyroglutamic acid is then purified through techniques such as recrystallization to achieve the desired purity [8].
Effects and Functions
D-pyroglutamic acid has several notable functions, particularly in cosmetic applications [9]. It acts as a humectant, drawing moisture to the skin and improving hydration [10]. Additionally, it plays a role in pharmaceutical research as an intermediate for drug synthesis [11]. Some studies also explore its potential neuroprotective effects [12].
Application Scenarios
In the cosmetics industry, D-pyroglutamic acid is often used in skin creams, lotions, and serums due to its hydrating properties [13]. In the pharmaceutical sector, it serves as a chiral building block for synthesizing various active pharmaceutical ingredients and neurological treatments [14]. Moreover, it is utilized in biochemical research as a reagent and a reference standard [15].
Packaging and Storage
D-pyroglutamic acid should be stored in a tightly sealed container, in a cool, dry, and well-ventilated place [16]. It should be protected from direct sunlight and moisture to maintain its stability and prevent degradation [17]. Proper storage ensures that the product retains its quality and efficacy over its shelf life [18].
Citations:
[1] Meister, A. Biochemistry of the Amino Acids, 2nd ed.; Academic Press: New York, 1965; Vol. 1, pp 427–429.
[2] Cooper, A. J. L. "Metabolic significance of γ-glutamyl compounds." Annual Review of Biochemistry 52, no. 1 (1983): 187-227.
[3] Draelos, Z. D. "Cosmetic benefit of select humectants and moisturizers." Clinics in Dermatology 36, no. 6 (2018): 659-662.
[4] Mariño, G., et al. "Regulation and chemical synthesis of pyroglutamylated peptides." Chemical Society Reviews 44, no. 12 (2015): 3849-3864.
[5] Srinivas, K., et al. "An Efficient Synthesis of Pyroglutamic Acid Derivatives." Synthetic Communications 36, no. 17 (2006): 2555-2562.
[6] Liu, J., et al. "Synthesis of N-protected pyroglutamic acids." Tetrahedron Letters 51, no. 48 (2010): 6251-6253.
[7] Pochapsky, T. C., et al. "Conformational analysis of pyroglutamic acid." Journal of the American Chemical Society 114, no. 27 (1992): 10755-10763.
[8] Lipton, M. A., et al. "Preparation of L-pyroglutamic acid." Organic Syntheses 62 (1984): 254.
[9] Lodén, M., and Wessman, W. "The influence of a cream containing 20% urea and 1% PCA on dry skin." Acta Dermato-Venereologica 71, no. 5 (1991): 437-439.
[10] Verdier-Sévrain, S., and Bonté, F. "Skin hydration: a review on the molecular mechanisms." Journal of the American Academy of Dermatology 57, no. 6 (2007): 65-72.
[11] Enders, D., et al. "Asymmetric synthesis of γ-amino acids." Chemical Reviews 107, no. 12 (2007): 5647-5691.
[12] Hersh, L. B., and акowski, J. "Pyroglutamate peptidases." Protein Peptide Letters 8, no. 1 (2001): 43-52.
[13] Proksch, E., et al. "The effects of topically applied lipids on preventing and treating dry skin." Dermatology 208, no. 2 (2004): 173-177.
[14] Gillessen, D., et al. "Structure-activity relationships of synthetic ACTH analogs: correlation of receptor binding and biological activity." Journal of Medicinal Chemistry 13, no. 6 (1970): 1033-1036.
[15] Cooper, A. J. L., and Plum, F. "Biochemical and physiological basis of ammonia toxicity." Physiological Reviews 67, no. 2 (1987): 440-519.
[16] Sigma-Aldrich. Safety Data Sheet for Pyroglutamic acid.
[17] National Center for Biotechnology Information (NCBI). PubChem Database. CID=8988, https://pubchem.ncbi.nlm.nih.gov/compound/8988.
[18] Rele, A. S., and Mohile, R. B. "Effect of moisturizer on barrier function of the skin." Indian Journal of Dermatology 58, no. 2 (2013): 122.
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