Isobutylparaben
(Synonyms: 尼泊金异丁酯,Isobutyl 4-hydroxybenzoate) 目录号 : GC63593
Isobutylparaben (Isobutyl 4-hydroxybenzoate) 是组成型雄烷受体 (CAR) 激活剂。Isobutylparaben 具有广谱抗菌 (antimicrobial) 活性，并广泛用于个人护理产品和化妆品中。
Cas No.:4247-02-3
Sample solution is provided at 25 µL, 10mM.
;)
,-1-7$$$37316672.jpg');)
;)
;)
$$$36806353.jpg');)
;33(7)%EF%BC%9A546-561$$$37156877.jpg');)
;)
;)
;)
%201124-1138.$$$35908550.jpg');)
%20766-780.$$$37100057.jpg');)
%20418-432.$$$36893736.jpg');)
%EF%BC%9A-240-255.$$$35108512.jpg');)
533-545$$$36543525.jpg');)
%201-13.$$$36600053.jpg');)
;)
Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Isobutylparaben (Isobutyl 4-hydroxybenzoate) is a constitutive androstane receptor (CAR) activator. Isobutylparaben has a broad-spectrum antimicrobial activity and widely used in personal care products and cosmetics[1].
[1]. Chieri Fujino, et al. Comparative Study of the Effect of 17 Parabens on PXR-, CAR- And PPARα-mediated Transcriptional Activation. Food Chem Toxicol. 2019 Nov;133:110792.
[2]. Fei Meng, et al. Isobutylparaben Negatively Affects Porcine Oocyte Maturation Through Increasing Oxidative Stress and Cytoskeletal Abnormalities. Environ Mol Mutagen. 2020 Apr;61(4):433-444.
| Cas No. | 4247-02-3 | SDF | |
| 别名 | 尼泊金异丁酯,Isobutyl 4-hydroxybenzoate | ||
| 分子式 | C11H14O3 | 分子量 | 194.23 |
| 溶解度 | DMSO : 100 mg/mL (514.85 mM; Need ultrasonic) | 储存条件 | Store at -20°C |
| 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。 |
||
| 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 | |||
 |
1 mg | 5 mg | 10 mg |
| 1 mM | 5.1485 mL | 25.7427 mL | 51.4854 mL |
| 5 mM | 1.0297 mL | 5.1485 mL | 10.2971 mL |
| 10 mM | 0.5149 mL | 2.5743 mL | 5.1485 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。
Final amended report on the safety assessment of Methylparaben, Ethylparaben, Propylparaben, Isopropylparaben, Butylparaben, Isobutylparaben, and Benzylparaben as used in cosmetic products
Int J Toxicol 2008;27 Suppl 4:1-82.PMID:19101832DOI:10.1080/10915810802548359.
Parabens is the name given to a group of p-hydroxybenzoic acid (PHBA) esters used in over 22,000 cosmetics as preservatives at concentrations up to 0.8% (mixtures of parabens) or up to 0.4% (single paraben). The group includes Methylparaben, Ethylparaben, Propylparaben, Isopropylparaben, Butylparaben, Isobutylparaben, and Benzylparaben. Industry estimates of the daily use of cosmetic products that may contain parabens were 17.76 g for adults and 378 mg for infants. Parabens in cosmetic formulations applied to skin penetrate the stratum corneum in inverse relation to the ester chain length. Carboxylesterases hydrolyze parabens in the skin. Parabens do not accumulate in the body. Serum concentrations of parabens, even after intravenous administration, quickly decline and remain low. Acute toxicity studies in animals indicate that parabens are not significantly toxic by various routes of administration. Subchronic and chronic oral studies indicate that parabens are practically nontoxic. Numerous genotoxicity studies, including Ames testing, dominant lethal assay, host-mediated assay, and cytogenic assays, indicate that the Parabens are generally nonmutagenic, although Ethylparaben and Methylparaben did increase chromosomal aberrations in a Chinese Hamster ovary cell assay. Ethylparaben, Propylparaben, and Butylparaben in the diet produced cell proliferation in the forestomach of rats, with the activity directly related to chain length of the alkyl chain, but Isobutylparaben and Butylparaben were noncarcinogenic in a mouse chronic feeding study. Methylparaben was noncarcinogenic when injected subcutaneously in mice or rats, or when administered intravaginally in rats, and was not cocarcinogenic when injected subcutaneously in mice. Propylparaben was noncarcinogenic in a study of transplacental carcinogenesis. Methylparaben was nonteratogenic in rabbits, rats, mice, and hamsters, and Ethylparaben was nonteratogenic in rats. Parabens, even at levels that produce maternal toxicity, do not produce fetal anomalies in animal studies. Parabens have been extensively studied to evaluate male reproductive toxicity. In one in vitro study, sperm were not viabile at concentrations as low as 6 mg/ml Methylparaben, 8 mg/ml Ethylparaben, 3 mg/ml Propylparaben, or 1 mg/ml Butylparaben, but an in vivo study of 0.1% or 1.0% Methylparaben or Ethylparaben in the diet of mice reported no spermatotoxic effects. Propylparaben did affect sperm counts at all levels from 0.01% to 1.0%. Epididymis and seminal vesicle weight decreases were reported in rats given a 1% oral Butylparaben dose; and decreased sperm number and motile activity in F(1) offspring of rats maternally exposed to 100 mg/kg day(- 1) were reported. Decreased sperm numbers and activity were reported in F(1) offspring of female rats given Butylparaben (in DMSO) by subcutaneous injection at 100 or 200 mg/kg day(- 1), but there were no abnormalities in the reproductive organs. Methylparaben was studied using rats at levels in the diet up to an estimated mean dose of 1141.1 mg/kg day(- 1) with no adverse testicular effects. Butylparaben was studied using rats at levels in the diet up to an estimated mean dose of 1087.6 mg/kg day(- 1) in a repeat of the study noted above, but using a larger number of animals and a staging analysis of testicular effects-no adverse reproductive effects were found. Butylparaben does bind to estrogen receptors in isolated rat uteri, but with an affinity orders of magnitude less than natural estradiol. Relative binding (diethylstilbesterol binding affinity set at 100) to the human estrogen receptors alpha and beta increases as a function of chain length from not detectable for Methylparaben to 0.267 +/- 0.027 for human estrogen receptor alpha and 0.340 +/- 0.031 for human estrogen receptor beta for Isobutylparaben. In a study of androgen receptor binding, Propylparaben exhibited weak competitive binding, but Methylparaben had no binding effect at all. PHBA at 5 mg/kg day(-1) subcutaneously (s.c.) was reported to produce an estrogenic response in one uterotrophic assay using mice, but there was no response in another study using rats (s.c. up to 5 mg/kg day(- 1)) and mice (s.c. up to 100 mg/kg day(- 1)) and in a study using rats (s.c. up to 100 mg/kg day(- 1)). Methylparaben failed to produce any effect in uterotrophic assays in two laboratories, but did produce an effect in other studies from another laboratory. The potency of Methylparaben was at least 1000x less when compared to natural estradiol. The same pattern was reported for Ethylparaben, Propylparaben, and Butylparaben when potency was compared to natural estradiol. In two studies, Isobutylparaben did produce an estrogenic response in the uterotrophic assay, but the potency was at least 240,000x less than estradiol. In one study, Benzylparaben produced an estrogenic response in the uterotrophic assay, but the potency was at least 330,000x less than estradiol. Estrogenic activity of parabens and PHBA was increased in human breast cancer cells in vitro, but the increases were around 4 orders of magnitude less than that produced by estradiol. Parabens are practically nonirritating and nonsensitizing in the population with normal skin. Paraben sensitization has occurred and continues to be reported in the case literature, but principally when exposure involves damaged or broken skin. Even when patients with chronic dermatitis are patch-tested to a parabens mix, parabens generally induce sensitization in less than 4% of such individuals. Many patients sensitized to paraben-containing medications can wear cosmetics containing these ingredients with no adverse effects. Clinical patch testing data available over the past 20 years demonstrate no significant change in the overall portion of dermatitis patients that test positive for parabens. As reviewed by the Cosmetic Ingredient Review (CIR) Expert Panel, the available acute, subchronic, and chronic toxicity tests, using a range of exposure routes, demonstrate a low order of parabens' toxicity at concentrations that would be used in cosmetics. Parabens are rarely irritating or sensitizing to normal human skin at concentrations used in cosmetics. Although parabens do penetrate the stratum corneum, metabolism of parabens takes place within viable skin, which is likely to result in only 1% unmetabolized parabens available for absorption into the body. The Expert Panel did consider data in the category of endocrine disruption, including male reproductive toxicity and various estrogenic activity studies. The CIR Expert Panel compared exposures to parabens resulting from use of cosmetic products to a no observed adverse effect level (NOAEL) of 1000 mg/kg day(- 1) based on the most statistically powerful and well-conducted study of the effects of Butylparabens on the male reproductive system. The CIR Expert Panel considered exposures to cosmetic products containing a single parabens preservative (use level of 0.4%) separately from products containing multiple parabens (use level of 0.8%) and infant exposures separately from adult exposures in determining margins of safety (MOS). The MOS for infants ranged from approximately 6000 for single paraben products to approximately 3000 for multiple paraben products. The MOS for adults ranged from 1690 for single paraben products to 840 for multiple paraben products. The Expert Panel considers that these MOS determinations are conservative and likely represent an overestimate of the possibility of an adverse effect (e.g., use concentrations may be lower, penetration may be less) and support the safety of cosmetic products in which parabens preservatives are used.
Isobutylparaben Negatively Affects Porcine Oocyte Maturation Through Increasing Oxidative Stress and Cytoskeletal Abnormalities
Environ Mol Mutagen 2020 Apr;61(4):433-444.PMID:31922297DOI:10.1002/em.22356.
As a member of parabens (PBs), Isobutylparaben (IBP) has a broad-spectrum antimicrobial activity and widely used in personal care products and cosmetics. Recent studies have indicated that usage of IBP poses a potential threat to reproductive health. In this study, we aimed to reveal the effects of acute exposure to IBP on the meiotic maturation of porcine cumulus oocyte complexes. Initial study showed that 200 μM of IBP significantly reduced the rate of the first polar body extrusion with no significant effect on cumulus cell expansion; however, 400 μM of IBP could significantly affect both. Further research revealed that abnormal spindles, misalignment chromosomes, and aberrant distributed actin filaments were detected in IBP-treated oocytes, which indicates that the cytoskeleton architecture of oocyte could be the target of IBP. At the same time, ROS level and apoptosis rate of oocyte were significantly increased by IBP exposure. Moreover, the levels of H3K9me3 and H3K27me3 were significantly induced in oocytes by IBP. Collectively, these results demonstrate that acute exposure to IBP could disrupt porcine oocyte maturation through affecting cytoskeleton, oxidative stress, viability and epigenetic modification. Environ. Mol. Mutagen. 2020. © 2020 Wiley Periodicals, Inc.
Oestrogenic activity of Isobutylparaben in vitro and in vivo
J Appl Toxicol 2002 Jul-Aug;22(4):219-26.PMID:12210538DOI:10.1002/jat.860.
The alkyl esters of p-hydroxybenzoic acid (parabens) are used widely as preservatives in foods, pharmaceuticals and cosmetics to which the human population is exposed. Recent studies have reported that methylparaben, ethylparaben, n-propylparaben and n-butylparaben all possess oestrogenic activity in several in vitro assays and in animal models in vivo. This study reports on the oestrogenic activity of Isobutylparaben in a panel of assays in vitro and in vivo. Isobutylparaben was able to displace [(3)H]oestradiol from cytosolic oestrogen receptor alpha of MCF7 human breast cancer cells by 81% at 100 000-fold molar excess. Using a clonal line of MCF7 cells containing a stably transfected oestrogen-responsive ERE-CAT reporter gene, CAT gene expression could be increased by Isobutylparaben such that the magnitude of the response was the same at 10(-5) M Isobutylparaben as with 10(-8) M 17beta-oestradiol. Isobutylparaben could also increase expression of the endogenous oestrogen-responsive pS2 gene in MCF7 cells and maximal expression at 10(-5) M Isobutylparaben could be inhibited with the anti-oestrogen ICI 182 780. The proliferation of two oestrogen-dependent human breast cancer cell lines MCF7 and ZR-75-1 could be increased with Isobutylparaben such that at concentrations of 10(-5) M the proliferation response was of the same magnitude as with 10(-8) M 17beta-oestradiol. Evidence for oestrogen receptor mediation of proliferation effects was provided by the inability of Isobutylparaben to influence the growth of oestrogen-unresponsive MDA-MB-231 human breast cancer cells and by the ability of the anti-oestrogen ICI 182 780 to inhibit the Isobutylparaben effects on MCF7 cell growth. The proliferation response to 10(-10) M 17beta-oestradiol was not antagonized with Isobutylparaben at any concentration from 10(-9) M to 10(-4) M in either MCF7 or ZR-75-1 cells. Finally, subcutaneous administration of Isobutylparaben was able to increase the uterine weight in the immature mouse after three daily doses of 1.2 or 12.0 mg per mouse. Previous work using linear-alkyl-chain parabens has shown that oestrogenic activity increases with alkyl chain length from methylparaben to n-butylparaben. The results here show that branching of the alkyl chain to Isobutylparaben increases oestrogenic activity beyond that of the equivalent length linear alkyl chain in n-butylparaben.
Reduction in semen quality after mixed exposure to bisphenol A and Isobutylparaben in utero and during lactation periods
Hum Exp Toxicol 2016 Aug;35(8):902-11.PMID:26519482DOI:10.1177/0960327115608927.
This study was performed to determine the effect of low-level exposure to a mixture of bisphenol A (BPA) and Isobutylparaben (IBP) on male reproduction. Corn oil, BPA (0.05 mg/kg/day), IBP (2.5 mg/kg/day), and a BPA/IBP mixture (BPA 0.05 mg/kg/day and IBP 2.5 mg/kg/day) were administered once daily by oral gavage to female rats for 5 weeks from gestation day 6 to lactation day 21. Male pups were killed at postnatal day 70 and examined for developmental characteristics, body weight, testis and epididymis weight, steroid hormones, epididymal sperm count and motility, and histological changes in testis and epididymis. The BPA/IBP mixture produced a significant downregulation of epididymal sperm count and motility. BPA or IBP alone also reduced epididymal sperm count and motility compared to control. These results indicate that exposure to low-level BPA/IBP mixture, which showed no notable physiological response in early life stages, can decrease semen quality in adulthood.
Toxicological evaluation of isopropylparaben and Isobutylparaben mixture in Sprague-Dawley rats following 28 days of dermal exposure
Regul Toxicol Pharmacol 2015 Nov;73(2):544-51.PMID:26359141DOI:10.1016/j.yrtph.2015.08.005.
The alkyl esters of p-hydroxybenzoic acid (Parabens) have been of concern due to their probable endocrine disrupting property especially in baby consumer products. The safety of parabens for use as a preservative in cosmetics has come into controversy, and thus consumer demand for paraben-free products is ever increasing. Thus, more comprehensive studies are needed to conclusively determine the safety of the multiple prolonged exposure to parabens with cosmetic ingredients. This study was conducted to investigate the potential repeated 28 days dermal toxicity (50, 100, 300, or 600 mg/kg bw/day) of isopropylparaben (IPP), Isobutylparaben (IBP), or the mixture of IPP and IBP in rats. There were no significant changes in body and organ weights in any group. However, histopathological examinations showed that weak or moderate skin damages were observed in female rats by macroscopic and microscopic evaluations. In female rats, no observed adverse effect levels (NOAELs) of IPP with no skin lesion and IBP for skin hyperkeratosis, were estimated to be 600 mg/kg bw/day, and 50 mg/kg bw/day, respectively. With regard skin hyperkeratosis, the lowest observed adverse effect level (LOAEL) of the mixture of IPP and IBP was estimated to be 50 mg/kg bw/day. Analysis of six serum hormones (estrogen, testosterone, insulin, T3, TSH, or FSH) in animals showed that only FSH was dose-dependently decreased in the mixture groups of 100 mg/kg bw/day or higher. These data suggest that the mixture of IPP and IBP showed a synergistic dermal toxicity in rats and should be considered for future use in consumer products.