A phenol with diverse biological activities
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Phloroglucinol

Item No. 23223

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
1,3,5-benzenetriol
CAS Number
108-73-6
Synonyms
  • Benzene-s-triol
  • 1,3,5-Hydroxybenzene
  • NSC 1572
  • 1,3,5-Trihydroxybenzene
  • sym-Trihydroxybenzene
Molecular Formula
C6H6O3
Formula Weight
126.1
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 30 mg/mlDMF:PBS(pH 7.2)(1:1): 0.5 mg/mlDMSO: 15 mg/mlEthanol: 25 mg/ml
λmax
226 nm
SMILES
OC1=CC(O)=CC(O)=C1
InChi Code
InChI=1S/C6H6O3/c7-4-1-5(8)3-6(9)2-4/h1-3,7-9H
InChi Key
QCDYQQDYXPDABM-UHFFFAOYSA-N
Shipping & Storage Information
Storage
4°C
Shipping
Room temperature in continental US; may vary elsewhere
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    25 g

    $37

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    Product Description

    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

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Achkar, J., Xian, M., Zhao, H., et al. Biosynthesis of phloroglucinol. J. 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 activation. J. 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 cells. Int. 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 transition. Cancer 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 Disease. PLoS One 10(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. 43, 423-437 (2016).

    7. de Jesus B. Cavalcante, M., Escoute, J., Madeira, J.P., et al. Reactive oxygen species and cellular interactions between Mycosphaerella fijiensis and banana. Trop. Plant. Biol. 4, 134-143 (2011).

    8. Singh, I.P., Sidana, J., Bharate, S.B., et al. Phloroglucinol compounds of natural origin: Synthetic aspects. Nat. 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 organs. Jpn. 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 study. Ailment Pharmacol. Ther. 25(9), 1115-1123 (2007).

    11. Tabassum, S., Afridi, B., and Aman, Z. Phloroglucinol for acceleration of labour: Double blind, randomized controlled trial. J. Pak. Med. Assoc. 55(7), 270-273 (2005).