Chlorphenesin
(Synonyms: 氯苯甘醚) 目录号 : GC60701
A synthetic preservative
Cas No.:104-29-0
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Chlorphenesin is a synthetic preservative.1 It is active against various strains of Pseudomonas and Burkholderia when used in combination with methylparaben (MICs = 5-10 g/L). Chlorphenesin (0.001-0.1%) is cytotoxic to immortalized human meibomian gland epithelial cells.2 It prevents homologous passive cutaneous anaphylaxis in rats (ID50 = 220 mg/kg).3 Formulations containing chlorphenesin have been used as biocides in cosmetic products.
1.Labadie, C., Cerutti, C., and Carlin, C.Fate and control of pathogenic and spoilage micro-organisms in orange blossom (Citrus aurantium) and rose flower (Rosa centifolia) hydrosolsJ. Appl. Microbiol.121(6)1568-1579(2016) 2.Wang, J., Liu, Y., Kam, W.R., et al.Toxicity of the cosmetic preservatives parabens, phenoxyethanol and chlorphenesin on human meibomian gland epithelial cellsExp. Eye Res.196108057(2020) 3.Koda, A., Nagai, H., Watanabe, S., et al.Inhibition of hypersensitivity reactions by a new drug, N(3’,4’-dimethoxycinnamoyl) anthranilic acid (N-5’)J. Allergy Clin. Immunol.57(5)396-407(1975)
| Cas No. | 104-29-0 | SDF | |
| 别名 | 氯苯甘醚 | ||
| Canonical SMILES | OCC(O)COC1=CC=C(Cl)C=C1 | ||
| 分子式 | C9H11ClO3 | 分子量 | 202.63 |
| 溶解度 | DMSO: 100 mg/mL (493.51 mM) | 储存条件 | 4°C, protect from light |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 4.9351 mL | 24.6755 mL | 49.351 mL |
| 5 mM | 0.987 mL | 4.9351 mL | 9.8702 mL |
| 10 mM | 0.4935 mL | 2.4676 mL | 4.9351 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Characterization of photoproducts and global ecotoxicity of Chlorphenesin: A preservative used in skin care products
Int J Cosmet Sci 2022 Feb;44(1):10-19.PMID:34958151DOI:10.1111/ics.12760.
Photolysis experiments of Chlorphenesin, used as a preservative in cosmetic products, were performed in aqueous solution and on a cream used in cosmetics. Three by-products resulting from the direct UV-visible photodegradation of Chlorphenesin were characterized by chromatography (gas and liquid) coupled with tandem mass spectrometry (GC-MS/MS and LC-HR MS/MS) and found in both solutions. In vitro tests on Vibrio fischeri bacteria showed that the overall ecotoxicity of Chlorphenesin increased with increasing irradiation time in both samples. In silico QSAR (Quantitative Structure Activity Relationship) tests were performed using T.E.S.T. (Toxicity Estimation Software Tool). Among the degradation compounds identified, 4-chlorophenol must contribute to the increased ecotoxicity of the photolyzed solution since the in silico LC50 estimated for all tests performed are always lower than those obtained for Chlorphenesin.
Chlorphenesin: an antigen-associated immunosuppressant
Infect Immun 1970 Jul;2(1):60-4.PMID:16557800DOI:10.1128/iai.2.1.60-64.1970.
Chlorphenesin (3-p-chlorophenoxy-1,2-propanediol), when injected intravenously together with either of two common bacterial antigens, inhibits the antibody response of the rabbit. The antigens studied are those common to Enterobacteriaceae and to gram-positive bacteria. The immunosuppression is contingent upon incubation of Chlorphenesin and antigen in vitro prior to administration, since separate injection of antigen and inhibitor or of mixtures without prior incubation yields undiminished antibody response. Chlorphenesin, as shown by hemagglutination-inhibition tests, does not alter the antigenic determinants, because antibody neutralization occurs in the presence or absence of the drug. The immunosuppressive effect is reversible, since precipitation of Chlorphenesin at 4 C substantially restores immunogenicity. Animals immunized with antigen-drug mixtures, which fail to respond with significant antibody production, nonetheless are immunologically primed. It is concluded that Chlorphenesin represents another example of antigen-associated immunosuppressants.
Safety Assessment of Chlorphenesin as Used in Cosmetics
Int J Toxicol 2014 May;33(2 suppl):5S-15S.PMID:24861369DOI:10.1177/1091581814526893.
Chlorphenesin functions as a biocide in cosmetics and is used at concentrations up to 0.32% in rinse-off products and up to 0.3% in leave-on products. The Cosmetic Ingredient Review Expert Panel (Panel) noted that Chlorphenesin was well absorbed when applied to the skin of rats; however, any safety concern was minimized because available data demonstrated an absence of toxicity. The Panel concluded that Chlorphenesin is safe in the present practices of use and concentration.
Toxicity of the cosmetic preservatives parabens, phenoxyethanol and Chlorphenesin on human meibomian gland epithelial cells
Exp Eye Res 2020 Jul;196:108057.PMID:32387382DOI:10.1016/j.exer.2020.108057.
Recently, we discovered that the cosmetic preservatives, benzalkonium chloride and formaldehyde, are especially toxic to human meibomian gland epithelial cells (HMGECs). Exposure to these agents, at concentrations approved for human use, leads within hours to cellular atrophy and death. We hypothesize that these effects are not unique, and that other cosmetic preservatives also exert adverse effects on HMGECs. Such compounds include parabens, phenoxyethanol and Chlorphenesin, which have been reported to be toxic to corneal and conjunctival epithelial cells, the liver and kidney, as well as to irritate the eye. To test our hypothesis, we examined the influence of parabens, phenoxyethanol and Chlorphenesin on the morphology, signaling, survival, proliferation and lipid expression of immortalized (I) HMGECs. These cells were cultured under proliferating or differentiating conditions with varying concentrations of methylparaben, ethylparaben, phenoxyethanol and Chlorphenesin for up to 5 days. We monitored the signaling ability, appearance, number and neutral lipid content of the IHMGECs, as well as their lysosome accumulation. Our findings show that a 30-min exposure of IHMGECs to these preservatives results in a significant reduction in the activity of the Akt pathway. This effect is dose-dependent and occurs at concentrations equal to (Chlorphenesin) and less than (all others) those dosages approved for human use. Further, a 24-h treatment of the IHMGECs with concentrations of methylparaben, ethylparaben, phenoxyethanol and Chlorphenesin close to, or at, the approved human dose induces cellular atrophy and death. At all concentrations tested, no preservative stimulated IHMGEC proliferation. Of particular interest, it was not possible to evaluate the influence of these preservatives, at close to human approved dosages, on IHMGEC differentiation, because the cells did not survive the treatment. In summary, our results support our hypothesis and show that methylparaben, ethylparaben, phenoxyethanol and Chlorphenesin are toxic to IHMGECs.
Chromatographic-mass spectrometric analysis of the urinary metabolite profile of Chlorphenesin observed after dermal application of chlorphenesin-containing sunscreen
Rapid Commun Mass Spectrom 2021 Dec 15;35(21):e9183.PMID:34431558DOI:10.1002/rcm.9183.
Rationale: Chlorphenesin is an approved biocide frequently used in cosmetics, and its carbamate ester is an approved skeletal muscle relaxant in certain countries for the treatment of discomfort related to skeletal muscle trauma and inflammation. A major urinary metabolite is 4-chlorophenoxy acetic acid (4-CPA), also known as para-chlorophenoxyacetate, which is also employed as a target analyte in sports drug testing to detect the use of the prohibited nootropic stimulant meclofenoxate. To distinguish between 4-CPA resulting from Chlorphenesin, Chlorphenesin carbamate, and meclofenoxate, urinary metabolite profiles of Chlorphenesin after legitimate use were investigated. Methods: Human administration studies with commercially available sunscreen containing 0.25% by weight of Chlorphenesin were conducted. Six study participants dermally applied 8 g of sunscreen and collected urine samples before and up to 7 days after application. Another set of six study participants applied 8 g of sunscreen on three consecutive days, and urine samples were also taken for up to 5 days after the last dosing. Urine specimens were analyzed using liquid chromatography-high resolution (tandem) mass spectrometry, and urinary metabolites were identified in accordance with literature data by accurate mass analysis of respective precursor and characteristic product ions. Results: In accordance with literature data, Chlorphenesin yielded the characteristic urinary metabolites, Chlorphenesin glucuronide, Chlorphenesin sulfate, and 3-(4-chlorophenoxy)-2-hydroxypropanoic acid (4-CPP), as well as the common metabolite 4-CPA. 4-CPA and 4-CPP were observed at similar abundances, with urinary concentrations of 4-CPA reaching up to ~1500 and 2300 ng/mL after single and multiple sunscreen applications, respectively. Conclusion: 4-CPA is a common metabolite of meclofenoxate, Chlorphenesin, and Chlorphenesin carbamate. Monitoring the diagnostic urinary metabolites of Chlorphenesin provides conclusive supporting evidence of whether Chlorphenesin or the prohibited nootropic meclofenoxate was administered.