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MedKoo Cat#: 528829 | Name: Pinocembrin (racemic)
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Description:

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

Pinocembrin, also known as DL-0108, is an androgen receptor ligand potentially for the treatment of acute stroke. Pinocembrin is a phenolic and flavonoid found in Manuka honey.

Chemical Structure

Pinocembrin (racemic)
Pinocembrin (racemic)
CAS#68745-38-0 (racemic)

Theoretical Analysis

MedKoo Cat#: 528829

Name: Pinocembrin (racemic)

CAS#: 68745-38-0 (racemic)

Chemical Formula: C15H12O4

Exact Mass: 256.0736

Molecular Weight: 256.26

Elemental Analysis: C, 70.31; H, 4.72; O, 24.97

Price and Availability

Size Price Availability Quantity
10mg USD 550.00 2 Weeks
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Related CAS #
480-39-7 (S-isomer) 68745-38-0 (racemic)
Synonym
DL-0108; DL0108; DL 0108; Pinocembrin
IUPAC/Chemical Name
5,7-dihydroxy-2-phenylchroman-4-one
InChi Key
URFCJEUYXNAHFI-UHFFFAOYSA-N
InChi Code
InChI=1S/C15H12O4/c16-10-6-11(17)15-12(18)8-13(19-14(15)7-10)9-4-2-1-3-5-9/h1-7,13,16-17H,8H2
SMILES Code
O=C1CC(C2=CC=CC=C2)OC3=C1C(O)=CC(O)=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
>2 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
Product Data
Product Data
Instruction
View handling instruction
Biological target:
(±)-Pinocembrin ((±)-5,7-Dihydroxyflavanone) is a GPR120 ligand able to promote wound healing in HaCaT cell line.
In vitro activity:
Preliminary studies, using a microbiological model of Klebsiella pneumoniae, provided first evidences that suggest Pinocembrin as a potential thermal stable inhibitor for HDC. Applying docking analysis revealed possible interaction between Pinocembrin and mammalian HDC. In vitro studies validated the predicted interaction and showed that Pinocembrin inhibits HDC activity and histamine in IgE-sensitized RBL-2H3 in response to dinitrophenol (DNP)-bovine serum albumin (BSA) stimulation. In addition, Pinocembrin mitigated the damage in the mitochondrial membrane, formation of cytoplasmic granules and degranulation as indicated by lower β-hexoseaminidase level. Reference: Eur J Pharmacol. 2017 Nov 5;814:178-186. https://pubmed.ncbi.nlm.nih.gov/28821452/
In vivo activity:
This study examined the protective effects and molecular mechanisms of pinocembrin in a murine model of SAH. Using an endovascular perforation model in rats, pinocembrin significantly mitigated SAH-induced neuronal tissue damage, including inflammatory injury and free-radical insults. Meanwhile, pinocembrin improved behavior function and reduced neuronal apoptosis. This study also revealed that sirtuin-1 (SIRT1) activation was significantly enhanced by pinocembrin. In addition, pinocembrin treatment evidently enhanced peroxisome proliferator-activated receptor-γ coactivator expression and suppressed ac-nuclear factor-kappa B levels. Reference: Oxid Med Cell Longev. 2022 Nov 16;2022:2242833. https://pubmed.ncbi.nlm.nih.gov/36439686/

Preparing Stock Solutions

The following data is based on the product molecular weight 256.26 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.

Recalculate based on batch purity %
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
Formulation protocol:
1. Li J, Li Y, Wang X, Xie Y, Lou J, Yang Y, Jiang S, Ye M, Chen H, Diao W, Xu S. Pinocembrin alleviates pyroptosis and apoptosis through ROS elimination in random skin flaps via activation of SIRT3. Phytother Res. 2023 May 7. doi: 10.1002/ptr.7864. Epub ahead of print. PMID: 37150741. 2. Hanieh H, Hairul Islam VI, Saravanan S, Chellappandian M, Ragul K, Durga A, Venugopal K, Senthilkumar V, Senthilkumar P, Thirugnanasambantham K. Pinocembrin, a novel histidine decarboxylase inhibitor with anti-allergic potential in in vitro. Eur J Pharmacol. 2017 Nov 5;814:178-186. doi: 10.1016/j.ejphar.2017.08.012. Epub 2017 Aug 15. PMID: 28821452. 3. Zeng Y, Fang Z, Lai J, Wu Z, Lin W, Yao H, Hu W, Chen J, Guo X, Chen X. Activation of Sirtuin-1 by Pinocembrin Treatment Contributes to Reduced Early Brain Injury after Subarachnoid Hemorrhage. Oxid Med Cell Longev. 2022 Nov 16;2022:2242833. doi: 10.1155/2022/2242833. PMID: 36439686; PMCID: PMC9683949. 4. Ran Q, Zhang C, Wan W, Ye T, Zou Y, Liu Z, Yu Y, Zhang J, Shen B, Yang B. Pinocembrin ameliorates atrial fibrillation susceptibility in rats with anxiety disorder induced by empty bottle stimulation. Front Pharmacol. 2022 Oct 20;13:1004888. doi: 10.3389/fphar.2022.1004888. PMID: 36339600; PMCID: PMC9631028.
In vitro protocol:
1. Li J, Li Y, Wang X, Xie Y, Lou J, Yang Y, Jiang S, Ye M, Chen H, Diao W, Xu S. Pinocembrin alleviates pyroptosis and apoptosis through ROS elimination in random skin flaps via activation of SIRT3. Phytother Res. 2023 May 7. doi: 10.1002/ptr.7864. Epub ahead of print. PMID: 37150741. 2. Hanieh H, Hairul Islam VI, Saravanan S, Chellappandian M, Ragul K, Durga A, Venugopal K, Senthilkumar V, Senthilkumar P, Thirugnanasambantham K. Pinocembrin, a novel histidine decarboxylase inhibitor with anti-allergic potential in in vitro. Eur J Pharmacol. 2017 Nov 5;814:178-186. doi: 10.1016/j.ejphar.2017.08.012. Epub 2017 Aug 15. PMID: 28821452.
In vivo protocol:
1. Zeng Y, Fang Z, Lai J, Wu Z, Lin W, Yao H, Hu W, Chen J, Guo X, Chen X. Activation of Sirtuin-1 by Pinocembrin Treatment Contributes to Reduced Early Brain Injury after Subarachnoid Hemorrhage. Oxid Med Cell Longev. 2022 Nov 16;2022:2242833. doi: 10.1155/2022/2242833. PMID: 36439686; PMCID: PMC9683949. 2. Ran Q, Zhang C, Wan W, Ye T, Zou Y, Liu Z, Yu Y, Zhang J, Shen B, Yang B. Pinocembrin ameliorates atrial fibrillation susceptibility in rats with anxiety disorder induced by empty bottle stimulation. Front Pharmacol. 2022 Oct 20;13:1004888. doi: 10.3389/fphar.2022.1004888. PMID: 36339600; PMCID: PMC9631028.
1: Zhu S, Cui M, Zhao Q. Characterization of the 2ODD genes of DOXC subfamily and its members involved in flavonoids biosynthesis in Scutellaria baicalensis. BMC Plant Biol. 2024 Aug 26;24(1):804. doi: 10.1186/s12870-024-05519-1. PMID: 39183318; PMCID: PMC11346219. 2: Main EN, Huang JC, Bowlin GL. Methyl Syringate: A Primary Driving Factor in Manuka Honeys Ability to Ameliorate Neutrophil Intracellular ROS Activity and NETosis. Front Biosci (Landmark Ed). 2024 Jul 19;29(7):255. doi: 10.31083/j.fbl2907255. PMID: 39082351. 3: Jorquera B, Valenzuela-Barra G, Mayorga A, Mejía J, Núñez G, Gómez M, Montenegro G, Vera Quezada WE, Echeverría J, Costa de Camargo A, Lino von Poser G, Bridi R. Exudate and Propolis from Escallonia pulverulenta: Phytochemical Characterization and Antibacterial Activity. Plants (Basel). 2024 Jul 19;13(14):1971. doi: 10.3390/plants13141971. PMID: 39065498; PMCID: PMC11281019. 4: Frattaruolo L, Lauria G, Aiello F, Carullo G, Curcio R, Fiorillo M, Campiani G, Dolce V, Cappello AR. Exploiting Glycyrrhiza glabra L. (Licorice) Flavanones: Licoflavanone's Impact on Breast Cancer Cell Bioenergetics. Int J Mol Sci. 2024 Jul 19;25(14):7907. doi: 10.3390/ijms25147907. PMID: 39063149; PMCID: PMC11276871. 5: Boreak N, Al Mahde RZ, Otayn WA, Alamer AY, Alrajhi T, Jafri S, Sharwani A, Swaidi E, Abozoah S, Mowkly AAM. Exploring Plant-Based Compounds as Alternatives for Targeting Enterococcus faecalis in Endodontic Therapy: A Molecular Docking Approach. Int J Mol Sci. 2024 Jul 15;25(14):7727. doi: 10.3390/ijms25147727. PMID: 39062969; PMCID: PMC11276846. 6: Zong YH, Cao JF, Zhao Y, Gao M, Chen WL, Wu M, Xu X, Xu ZY, Zhang XQ, Tang JZ, Liu Y, Hu XS, Wang SQ, Zhang X. Mechanism of Lian Hua Qing Wen capsules regulates the inflammatory response caused by M1 macrophage based on cellular experiments and computer simulations. Acta Trop. 2024 Sep;257:107320. doi: 10.1016/j.actatropica.2024.107320. Epub 2024 Jul 14. PMID: 39002739. 7: Schulz M, Gonzaga LV, Antunes ACN, Lubschinski T, Mohr ETB, Dalmarco EM, Deolindo CTP, Hoff RB, Zambonim FM, Costa ACO, Fett R. The Protective Effect of Juçara Fruit (Euterpe edulis Martius) Extracts on LPS-Activated J774 Macrophages. Plant Foods Hum Nutr. 2024 Jul 8. doi: 10.1007/s11130-024-01204-8. Epub ahead of print. PMID: 38976202. 8: Ji X, Li L, Zhang K, Yuan X, Li Q, Bai G. Screening and analysis of the targeted compounds in Choerospondias axillaris extract by receptor chromatographic column with immobilized angiotensin II type 1 receptor. Biomed Chromatogr. 2024 Aug;38(8):e5931. doi: 10.1002/bmc.5931. Epub 2024 Jun 16. PMID: 38881185. 9: Hou M, Tian H, Wu J, Deng Z. Metabolite identification and excretion of pinocembrin-7-O-β-D-glucoside in rats by UHPLC/MS. J Pharm Biomed Anal. 2024 Sep 15;248:116291. doi: 10.1016/j.jpba.2024.116291. Epub 2024 Jun 6. PMID: 38852297. 10: Kolayli S, Can Z, Kara Y, Ozkok A, Ozmert Ergin S, Kemal M, Demir Kanbur E. Physicochemical Characteristics, Phenolic Components, and Antioxidant Capacities of Lavender Honey (Lavandula Spp.) from Isparta Region of Türkiye. Chem Biodivers. 2024 Jun 6:e202400718. doi: 10.1002/cbdv.202400718. Epub ahead of print. PMID: 38843376. 11: Ali BM, Al-Mokaddem AK, Selim HMRM, Alherz FA, Saleh A, Hamdan AME, Ousman MS, El-Emam SZ. Pinocembrin's protective effect against acute pancreatitis in a rat model: The correlation between TLR4/NF-κB/NLRP3 and miR-34a-5p/SIRT1/Nrf2/HO-1 pathways. Biomed Pharmacother. 2024 Jul;176:116854. doi: 10.1016/j.biopha.2024.116854. Epub 2024 Jun 1. PMID: 38824834. 12: Liu R, Li JZ, Song JK, Zhou D, Huang C, Bai XY, Xie T, Zhang X, Li YJ, Wu CX, Zhang L, Li L, Zhang TT, Du GH. Corrigendum to: "Pinocembrin improves cognition and protects the neurovascular unit in Alzheimer related deficits" [Neurobiol. Aging 35 (2014) 1275-1285]. Neurobiol Aging. 2024 May 22:S0197-4580(24)00101-5. doi: 10.1016/j.neurobiolaging.2024.05.010. Epub ahead of print. Erratum for: Neurobiol Aging. 2014 Jun;35(6):1275-85. doi: 10.1016/j.neurobiolaging.2013.12.031. PMID: 38782666. 13: Zhang J, Ye L, Chen Q, Wang F. Response analysis of Pinus sibirica to pine wood nematode infection through transcriptomics and metabolomics study. Front Plant Sci. 2024 May 7;15:1383018. doi: 10.3389/fpls.2024.1383018. PMID: 38774221; PMCID: PMC11106439. 14: Wei C, Wu Z, Yang X, Jiang X, Wang L, He J, Tong G. Integrating Network Pharmacology and In Vitro Experiments for Assessing the Anti-Tumor Effects of Phyllanthus Urinaria L Anti-neoplastic Decoction in Hepatocellular Carcinoma. Altern Ther Health Med. 2024 May 17:AT10123. Epub ahead of print. PMID: 38758152. 15: El-Kersh DM, Abou El-Ezz RF, Ramadan E, El-Kased RF. In vitro and in vivo burn healing study of standardized propolis: Unveiling its antibacterial, antioxidant and anti-inflammatory actions in relation to its phytochemical profiling. PLoS One. 2024 May 14;19(5):e0302795. doi: 10.1371/journal.pone.0302795. PMID: 38743731; PMCID: PMC11093344. 16: Ionus E, Schröder V, Chiţescu CL, Bucur LA, Lupu CE, Dumitrescu DE, Popescu L, Mihai DP, Olaru OT, Nițulescu GM, Boscencu R, Gîrd CE. Phytochemical, In Vitro, In Vivo, and In Silico Research on the Extract of Ajuga chamaepitys (L.) Schreb. Plants (Basel). 2024 Apr 25;13(9):1192. doi: 10.3390/plants13091192. PMID: 38732407; PMCID: PMC11085171. 17: Hong G, Li S, Zheng G, Zheng X, Zhan Q, Zhou L, Wei Q, He W, Chen Z. Therapeutic potential of a prominent dihydroxyflavanone pinocembrin for osteolytic bone disease: In vitro and in vivo evidence. J Orthop Translat. 2024 Mar 27;45:197-210. doi: 10.1016/j.jot.2023.12.007. PMID: 38685969; PMCID: PMC11056316. 18: Mergen Duymaz G, Duz G, Ozkan K, Karadag A, Yilmaz O, Karakus A, Cengiz O, Akyildiz IE, Basdogan G, Damarlı E, Sagdic O. The evaluation of L-arginine solution as a solvent for propolis extraction: The phenolic profile, antioxidant, antibacterial activity, and in vitro bioaccessibility. Food Sci Nutr. 2024 Jan 11;12(4):2724-2735. doi: 10.1002/fsn3.3953. PMID: 38628177; PMCID: PMC11016385. 19: Zagórska J, Pietrzak K, Kukula-Koch W, Czop M, Wojtysiak K, Koch W. Influence of Thermal Treatment on the Composition of Alpinia officinarum Rhizome. Int J Mol Sci. 2024 Mar 24;25(7):3625. doi: 10.3390/ijms25073625. PMID: 38612437; PMCID: PMC11012154. 20: Saroglu O, Karadag A. Propolis-loaded liposomes: characterization and evaluation of the in vitro bioaccessibility of phenolic compounds. ADMET DMPK. 2024 Feb 5;12(1):209-224. doi: 10.5599/admet.2204. PMID: 38560718; PMCID: PMC10974815.