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4-Methylbenzylidene camphor Catalog No.GC11606

ultraviolet light blocker used in cosmetics and sunscreen preparations that also has estrogenic activities.

Size Price Stock Qty
10mM (in 1mL DMSO)
$37.00
In stock
1g
$71.00
In stock
5g
$331.00
In stock
10g
$536.00
In stock

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Sample solution is provided at 25 µL, 10mM.

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Chemical Properties

Cas No. 36861-47-9 SDF
Synonyms 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 For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
Shipping Condition Evaluation sample solution : ship with blue ice
All other available size: ship with RT , or blue ice upon request
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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).