Terphenyllin | CAS#52452-60-5 | p-terphenyl metabolite

MedKoo Cat#: 330219 | Name: Terphenyllin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Terphenyllin is a naturally abundant p-terphenyl metabolite isolated from the coral derived fungus Aspergillus candidus, has signiﬁcant α-glucosidase inhibitory activity.

Chemical Structure

Terphenyllin

CAS#52452-60-5

Theoretical Analysis

MedKoo Cat#: 330219

Name: Terphenyllin

CAS#: 52452-60-5

Chemical Formula: C20H18O5

Exact Mass: 338.1154

Molecular Weight: 338.36

Elemental Analysis: C, 71.00; H, 5.36; O, 23.64

Price and Availability

Size	Price	Availability
25mg	USD 750.00	2 Weeks
50mg	USD 1,250.00	2 Weeks
100mg	USD 1,950.00	2 Weeks
200mg	USD 3,250.00	2 Weeks

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Related CAS #

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Synonym

Terphenyllin

IUPAC/Chemical Name

3',6'-dimethoxy-[1,1':4',1''-terphenyl]-2',4,4''-triol

InChi Key

YNEMPXKRLPZFAX-UHFFFAOYSA-N

InChi Code

InChI=1S/C20H18O5/c1-24-17-11-16(12-3-7-14(21)8-4-12)20(25-2)19(23)18(17)13-5-9-15(22)10-6-13/h3-11,21-23H,1-2H3

SMILES Code

OC1=C(OC)C(C2=CC=C(O)C=C2)=CC(OC)=C1C3=CC=C(O)C=C3

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 338.36 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

1: Wu W, Wu MY, Dai T, Ke LN, Shi Y, Hu J, Wang Q. Terphenyllin induces CASP3-dependent apoptosis and pyroptosis in A375 cells through upregulation of p53. Cell Commun Signal. 2024 Aug 21;22(1):409. doi: 10.1186/s12964-024-01784-7. PMID: 39169379; PMCID: PMC11337594. 2: Zeng Y, Wang S, Peng H, Zhao W, Chang W, Wang H, Chen H, Dai H. p-Terphenyl and Diphenyl Ether Derivatives from the Marine-Derived Fungus Aspergillus candidus HM5-4. Mar Drugs. 2023 Dec 24;22(1):13. doi: 10.3390/md22010013. PMID: 38248638; PMCID: PMC10817493. 3: Cao XZ, Zhang BQ, Wang CF, Yin JN, Haider W, Said G, Wei MY, Lu L. A Terphenyllin Derivative CHNQD-00824 from the Marine Compound Library Induced DNA Damage as a Potential Anticancer Agent. Mar Drugs. 2023 Sep 27;21(10):512. doi: 10.3390/md21100512. PMID: 37888447; PMCID: PMC10608154. 4: Guo Z, Abulaizi A, Huang L, Xiong Z, Zhang S, Liu T, Wang R. Discovery of p-Terphenyl Metabolites as Potential Phosphodiesterase PDE4D Inhibitors from the Coral-Associated Fungus Aspergillus sp. ITBBc1. Mar Drugs. 2022 Oct 28;20(11):679. doi: 10.3390/md20110679. PMID: 36355001; PMCID: PMC9696254. 5: Wei S, Chen YS, Shi Y. Metabolomic profiling of exhaled breath condensate for the diagnosis of pulmonary aspergillosis. Front Cell Infect Microbiol. 2022 Sep 8;12:1008924. doi: 10.3389/fcimb.2022.1008924. PMID: 36159648; PMCID: PMC9492867. 6: Bailly C. Anti-inflammatory and anticancer p-terphenyl derivatives from fungi of the genus Thelephora. Bioorg Med Chem. 2022 Sep 15;70:116935. doi: 10.1016/j.bmc.2022.116935. Epub 2022 Jul 21. PMID: 35901638. 7: Yu D, Qi S, Guan X, Yu W, Yu X, Cai M, Li Q, Wang W, Zhang W, Qin JJ. Inhibition of STAT3 Signaling Pathway by Terphenyllin Suppresses Growth and Metastasis of Gastric Cancer. Front Pharmacol. 2022 Mar 25;13:870367. doi: 10.3389/fphar.2022.870367. PMID: 35401187; PMCID: PMC8993145. 8: Haider W, Xu WF, Liu M, Wu YW, Tang YF, Wei MY, Wang CY, Lu L, Shao CL. Structure-Activity Relationships and Potent Cytotoxic Activities of Terphenyllin Derivatives from a Small Compound Library. Chem Biodivers. 2020 Jul;17(7):e2000207. doi: 10.1002/cbdv.202000207. Epub 2020 Jun 17. PMID: 32367656. 9: Zhang J, Wang W, Zhou Y, Yang J, Xu J, Xu Z, Xu B, Yan L, Cheng XD, Li M, Qin JJ. Terphenyllin Suppresses Orthotopic Pancreatic Tumor Growth and Prevents Metastasis in Mice. Front Pharmacol. 2020 Apr 8;11:457. doi: 10.3389/fphar.2020.00457. PMID: 32322210; PMCID: PMC7157903. 10: Shan T, Wang Y, Wang S, Xie Y, Cui Z, Wu C, Sun J, Wang J, Mao Z. A new p-terphenyl derivative from the insect-derived fungus Aspergillus candidus Bdf-2 and the synergistic effects of terphenyllin. PeerJ. 2020 Jan 2;8:e8221. doi: 10.7717/peerj.8221. PMID: 31915570; PMCID: PMC6942676. 11: Zhang XQ, Mou XF, Mao N, Hao JJ, Liu M, Zheng JY, Wang CY, Gu YC, Shao CL. Design, semisynthesis, α-glucosidase inhibitory, cytotoxic, and antibacterial activities of p-terphenyl derivatives. Eur J Med Chem. 2018 Feb 25;146:232-244. doi: 10.1016/j.ejmech.2018.01.057. Epub 2018 Feb 4. PMID: 29407953. 12: Wang W, Liao Y, Tang C, Huang X, Luo Z, Chen J, Cai P. Cytotoxic and Antibacterial Compounds from the Coral-Derived Fungus Aspergillus tritici SP2-8-1. Mar Drugs. 2017 Nov 7;15(11):348. doi: 10.3390/md15110348. PMID: 29112138; PMCID: PMC5706038. 13: Guo ZK, Yan T, Guo Y, Song YC, Jiao RH, Tan RX, Ge HM. p-Terphenyl and diterpenoid metabolites from endophytic Aspergillus sp. YXf3. J Nat Prod. 2012 Jan 27;75(1):15-21. doi: 10.1021/np200321s. Epub 2011 Dec 23. PMID: 22196792. 14: Singh SB, Jayasuriya H, Dewey R, Polishook JD, Dombrowski AW, Zink DL, Guan Z, Collado J, Platas G, Pelaez F, Felock PJ, Hazuda DJ. Isolation, structure, and HIV-1-integrase inhibitory activity of structurally diverse fungal metabolites. J Ind Microbiol Biotechnol. 2003 Dec;30(12):721-31. doi: 10.1007/s10295-003-0101-x. Epub 2004 Jan 9. PMID: 14714192. 15: Yen GC, Chiang HC, Wu CH, Yeh CT. The protective effects of Aspergillus candidus metabolites against hydrogen peroxide-induced oxidative damage to Int 407 cells. Food Chem Toxicol. 2003 Nov;41(11):1561-7. doi: 10.1016/s0278-6915(03)00174-1. PMID: 12963009. 16: Yen GC, Chang YC, Sheu F, Chiang HC. Isolation and characterization of antioxidant compounds from Aspergillus candidus broth filtrate. J Agric Food Chem. 2001 Mar;49(3):1426-31. doi: 10.1021/jf001109t. PMID: 11312875. 17: Rahbaek L, Frisvad JC, Christophersen C. An amendment of Aspergillus section Candidi based on chemotaxonomical evidence. Phytochemistry. 2000 Mar;53(5):581-6. doi: 10.1016/s0031-9422(99)00596-8. PMID: 10724184. 18: Kamigauchi T, Sakazaki R, Nagashima K, Kawamura Y, Yasuda Y, Matsushima K, Tani H, Takahashi Y, Ishii K, Suzuki R, Koizumi K, Nakai H, Ikenishi Y, Terui Y. Terprenins, novel immunosuppressants produced by Aspergillus candidus. J Antibiot (Tokyo). 1998 Apr;51(4):445-50. doi: 10.7164/antibiotics.51.445. PMID: 9630870. 19: Kurobane I, Vining LC, McInnes AG, Smith DG. 3-Hydroxyterphenyllin, a new metabolite of Aspergillus candidus. Structure elucidation by H and C nuclear magnetic resonance spectroscopy. J Antibiot (Tokyo). 1979 Jun;32(6):559-64. doi: 10.7164/antibiotics.32.559. PMID: 468731. 20: Ohtsubo K, Saito M. Hepato-and cardiotoxicity of xanthoascin, a new xanthocillin analogue produced by Aspergillus candidus. II. A preliminary electron microscopic observation of the heart and lung with intranuclear myelin- like figures. Ann Nutr Aliment. 1977;31(4-6):771-80. PMID: 613931.