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4-Methylbenzylidene camphor (Synonyms: Enzacamene|Eusolex 6300|4-MBC|Neo Heliopan MBC|Parsol 500|Uvinul MBC 95)

Catalog No.GC11606

Le 4-méthylbenzylidène camphre (4-MBC; Enzacamène) est un dérivé de camphre organique utilisé dans l'industrie cosmétique pour sa capacité À protéger la peau contre les UV, en particulier les rayons UV B.

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4-Methylbenzylidene camphor Chemical Structure

Cas No.: 36861-47-9

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10mM (in 1mL DMSO)
31,00 $US
En stock
1g
60,00 $US
En stock
5g
277,00 $US
En stock
10g
449,00 $US
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Sample solution is provided at 25 µL, 10mM.

Product Documents

Quality Control & SDS

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Background

4-Methylbenzylidene camphor (4-MBC) is an ultraviolet light blocker used in cosmetics and sunscreen preparations that also has estrogenic activities.

Since the estrogen receptor (ER) ligand type can influence transactivation, it is important to obtain information on molecular actions of nonclassical ER agonists.

In vitro: Previous results of competitive binding assays using cytosolic protein preparations from Xenopus hepatocytes demonstrated that 4-MBC could weakly bind to the ER. In addition, 4-MBC at a 100 micromol/L was not able to replace estradiol from the receptor completely [1].

In vivo: The estrogen target gene expression in uterus of Long Evans rats after exposure to 4-MBC was studied. Results showed that 4-MBC could altere steady-state levels of mRNAs encoding for ER, progesterone receptor (PR), and androgen recepto in uterus of 12-wk-old offspring. To evaluate sensitivity to estradiol (E2), offspring were injected with E2, and killed 6 h later. Acute up-regulation of PR and IGF-I and down-regulation of ER and androgen receptor by E2 were reduced in 4-MBC treated rats dose-dependently [2].

Clinical trial: In a 2-week single-blinded study, 15 young males and 17 postmenopausal females, were assigned to daily whole-body topical application of 2 mg per cm2 of 4-MBC basic cream formulation. Maximum plasma concentrations were 20 ng/mL for both females and men. 4-MBC was detectable in urine. The reproductive hormones FSH, LH were unchanged but minor differences in testosterone levels were observed between the 2 wk [3].

References:
[1] Klann A, Levy G, Lutz I, Müller C, Kloas W, Hildebrandt JP.  Estrogen-like effects of ultraviolet screen 3-(4-methylbenzylidene)-camphor (Eusolex 6300) on cell proliferation and gene induction in mammalian and amphibian cells. Environ Res. 2005 Mar;97(3):274-81.
[2] S.  Durrer, K. Maerkel, M. Schlumpf, et al. Estrogen target gene regulation and coactivator expression in rat uterus after developmental exposure to the ultraviolet filter 4-methylbenzylidene camphor. Endocrinology 146(5), 2130-2139 (2005).
[3] N.  R. Janjua, B. Mogensen, A. M. Andersson, et al. Systemic absorption of the sunscreens benzophenone-3, octyl-methoxycinnamate, and 3-(4-methyl-benzylidene) camphor after whole-body topical application and reproductive hormone levels in humans. Journal of Investigative Dermatology 123, 57-61(2004).

Chemical Properties

Cas No. 36861-47-9 SDF
Synonymes Enzacamene|Eusolex 6300|4-MBC|Neo Heliopan MBC|Parsol 500|Uvinul MBC 95
Chemical Name 1,7,7-trimethyl-3-[(4-methylphenyl)methylene]-bicyclo[2.2.1]heptan-2-one
Canonical SMILES CC1=CC=C(/C=C2[C@H]3CC[C@@](C)(C3(C)C)C/2=O)C=C1
Formula C18H22O M.Wt 254.4
Solubility ≥ 10mg/mL in DMSO Storage Store at -20°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table

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1 mg 5 mg 10 mg
1 mM 3.9308 mL 19.6541 mL 39.3082 mL
5 mM 0.7862 mL 3.9308 mL 7.8616 mL
10 mM 0.3931 mL 1.9654 mL 3.9308 mL
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Average Rating: 5 ★★★★★ (Based on Reviews and 10 reference(s) in Google Scholar.)

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