Phloroglucinol
(Synonyms: 间苯三酚) 目录号 : GC47955
A phenol with diverse biological activities
Cas No.:108-73-6
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
Phloroglucinol is a naturally occurring phenol that exhibits diverse biological activities.1 Phloroglucinol protects V79-4 Chinese hamster lung fibroblast cells from oxidative stress and inhibits lipid peroxidation by scavenging reactive oxygen species (ROS).2 It induces apoptosis in HT-29 human colon cancer cells and inhibits metastasis of BT549 and MDA-MB-231 human breast cancer cells.3,4 Phloroglucinol protects primary neurons from β-amyloid-induced dendritic spine loss in vitro and shortens the latency to find the platform in a Morris water maze test in an Alzheimer's disease (AD) mouse model.5 Phloroglucinol has been used to stain histological plant sections and in the synthesis of numerous natural products.6,7,8 Phloroglucinol slows the frequency and decreases the amplitude of contraction in isolated rabbit and rat intestine at a concentration of 100 and 1 μM, respectively.9 Formulations containing phloroglucinol have been used as antispasmodics.10,11
1.Achkar, J., Xian, M., Zhao, H., et al.Biosynthesis of phloroglucinolJ. Am. Chem. Soc.127(15)5332-5333(2005) 2.Kang, K.A., KLee, K.H., Chae, S., et al.Cytoprotective effect of phloroglucinol on oxidative stress induced cell damage via catalase activationJ. Cell. Biochem.97(3)609-620(2006) 3.Kang, M.-H., Kim, I.-H., and Nam, T.-J.Phloroglucinol induces apoptosis through the regulation of insulin-like growth factor 1 receptor signaling pathways in human colon cancer HT-29 cellsInt. J. Oncol.45(3)1036-1042(2014) 4.Kim, R.-K., Suh, Y., Yoo, K.-C., et al.Phloroglucinol suppresses metastatic ability of breast cancer cells by inhibition of epithelial-mesenchymal cell transitionCancer Sci.106(1)94-101(2015) 5.Yang, E.-J., Ahn, S., Ryu, J., et al.Phloroglucinol attenuates the cognitive deficits of the 5XFAD mouse model of Alzheimer's DiseasePLoS One10(8)eD135686(2015) 6.KholovÁ, J., Zindy, P., Malayee, S., et al.Component traits of plant water use are modulated by vapour pressure deficit in pearl millet (Pennisetum glaucum (L.) R.Br.)Func. Plant. Bio.43423-437(2016) 7.de Jesus B. Cavalcante, M., Escoute, J., Madeira, J.P., et al.Reactive oxygen species and cellular interactions between Mycosphaerella fijiensis and bananaTrop. Plant. Biol.4134-143(2011) 8.Singh, I.P., Sidana, J., Bharate, S.B., et al.Phloroglucinol compounds of natural origin: Synthetic aspectsNat. Prod. Rep.27(3)393-416(2010) 9.Inoue, S.Effects of 1,3,5-trihydroxybenzene and 2,4,6-trihydroxy-1-propiophenone on the smooth muscle organsJpn. J. Pharmacol.19(2)224-233(1969) 10.Chassany, O., Bonaz, B., Bruley DES Varannes, S., et al.Acute exacerbation of pain in irritable bowel syndrome: efficacy of phloroglucinol/trimethylphloroglucinol. A randomized, double-blind, placebo-controlled studyAilment Pharmacol. Ther.25(9)1115-1123(2007) 11.Tabassum, S., Afridi, B., and Aman, Z.Phloroglucinol for acceleration of labour: Double blind, randomized controlled trialJ. Pak. Med. Assoc.55(7)270-273(2005)
| Cas No. | 108-73-6 | SDF | |
| 别名 | 间苯三酚 | ||
| Canonical SMILES | OC1=CC(O)=CC(O)=C1 | ||
| 分子式 | C6H6O3 | 分子量 | 126.1 |
| 溶解度 | DMF: 30 mg/ml,DMF:PBS(pH 7.2)(1:1): 0.5 mg/ml,DMSO: 15 mg/ml,Ethanol: 25 mg/ml | 储存条件 | Store at RT |
| 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 | 7.9302 mL | 39.6511 mL | 79.3021 mL |
| 5 mM | 1.586 mL | 7.9302 mL | 15.8604 mL |
| 10 mM | 0.793 mL | 3.9651 mL | 7.9302 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。
Structural Diversity of Complex Phloroglucinol Derivatives from Eucalyptus Species
Chem Biodivers 2022 Jun;19(6):e202200025.PMID:35621714DOI:10.1002/cbdv.202200025.
Several species of the genus Eucalyptus are used in many traditional medicine systems for the treatment of respiratory tract infections, colds, flu, sore throats, and bronchitis. The genus Eucalyptus (Myrtaceae) is a well-known natural source of bioactive phloroglucinols. These polyphenolic compounds bear an aromatic phenyl ring with three hydroxy groups (1,3,5-trihydroxybenzene) which have been exhibiting a variety of biological activities such as antimicrobial, anticancer, anti-allergic, anti-inflammatory, and antioxidant activities. This review summarizes the literature published from 1997 until the end of 2021 and addresses the structure diversity of phloroglucinols isolated from Eucalyptus species and their biological activities. Phloroglucinol-terpene adducts are the main class of compounds that have been reported in this genus.
Phloroglucinol compounds of therapeutic interest: global patent and technology status
Expert Opin Ther Pat 2009 Jun;19(6):847-66.PMID:19473105DOI:10.1517/13543770902916614.
Background: Phloroglucinol compounds, both synthetic as well as natural, have shown a vast array of biological activities. There are a wide range of applications of Phloroglucinol compounds in pharmaceuticals, cosmetics, textiles, paints and dyeing industries. Although many of the phloroglucinols have shown promising results in various biological assays, very few have reached clinics. Objective: To compile the patented information on various therapeutically active Phloroglucinol molecules, so that technologies used in isolation and activity assessment of these compounds could be unearthed and the compiled information be utilized for further development of these molecules. Methods: The European Patent Office database (official website: espacenet.com) was searched with a keyword "Phloroglucinol". In addition, patents were searched using names of compounds listed in our previous review. Conclusions: This class holds potential for development of molecules in various therapeutic areas. There exist a number of patents on preparations that have Phloroglucinol compounds as active ingredient(s). Many such preparations have been tested in vitro and/or in vivo for their efficacy and proven to be active and non-toxic. Commercialization of existing technology on Phloroglucinol molecules can yield fruitful results.
Recent advances in the synthesis of natural products containing the Phloroglucinol motif
Nat Prod Rep 2022 Sep 21;39(9):1766-1802.PMID:35762867DOI:10.1039/d1np00077b.
Covering: June 2009 to 2021Natural products containing a Phloroglucinol motif include simple and oligomeric phloroglucinols, polycyclic polyprenylated acylphloroglucinols, phloroglucinol-terpenes, xanthones, flavonoids, and coumarins. These compounds represent a major class of secondary metabolites which exhibit a wide range of biological activities such as antimicrobial, anti-inflammatory, antioxidant and hypoglycaemic properties. A number of these compounds have been authorized for therapeutic use or are currently being studied in clinical trials. Their structural diversity and utility in both traditional and conventional medicine have made them popular synthetic targets over the years. In this review, we compile and summarise the recent synthetic approaches to the natural products bearing a Phloroglucinol motif. Focus has been given on ingenious strategies to functionalize the Phloroglucinol moiety at multiple positions. The isolation and bioactivities of the compounds are also provided.
Phloroglucinol derivatives rhotomensones A-G from Rhodomyrtus tomentosa
Phytochemistry 2021 Oct;190:112890.PMID:34388480DOI:10.1016/j.phytochem.2021.112890.
Undescribed Phloroglucinol derivatives, rhotomensones A-G, and a known derivative rhodomyrtosone B, were isolated from the leaves of Rhodomyrtus tomentosa. Rhotomensones A-D and G have unreported structural characteristics, in which rhotomensone A substitutes a benzene ring, rhotomensones B-D are bonded with a 2-methylbutanoyl group, and rhotomensone G has two fewer carbons. The structures of these compounds were determined by NMR spectroscopy, circular dichroism (CD) spectroscopy and X-ray crystallography. The inhibitory activities against α-glucosidase of rhotomensones E and F were evaluated in vitro, with IC50 values of 0.50 ± 0.14 mg/mL and 0.07 ± 0.02 mg/mL. Moreover, rhodomyrtosone B showed significant antibacterial activity against some bacteria, with MIC values ranging from 0.50 to 16.00 μg/mL.
Phloroglucinol compounds of natural origin: synthetic aspects
Nat Prod Rep 2010 Mar;27(3):393-416.PMID:20179878DOI:10.1039/b914364p.
This review covers the synthetic aspects of various naturally occurring phloroglucinols, describing syntheses of 42 compounds and citing 137 references.