MedKoo Cat#: 585016 | Name: Plastoquinone

Description:

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

Plastoquinone is a polyunsaturated side-chain quinone derivative which is an important link in the electron transport chain of green plants during the photosynthetic conversion of light energy by photophosphorylation into the potential energy of chemical bonds.

Chemical Structure

Plastoquinone
Plastoquinone
CAS#4299-57-4

Theoretical Analysis

MedKoo Cat#: 585016

Name: Plastoquinone

CAS#: 4299-57-4

Chemical Formula: C53H80O2

Exact Mass: 748.6158

Molecular Weight: 749.22

Elemental Analysis: C, 84.97; H, 10.76; O, 4.27

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
Bulk Inquiry
Related CAS #
No Data
Synonym
Plastoquinone; Q 254; Q254; Q-254
IUPAC/Chemical Name
2,5-Cyclohexadiene-1,4-dione, 2,3-dimethyl-5-(3,7,11,15,19,23,27,31,35-nonamethyl-2,6,10,14,18,22,26,30,34-hexatriacontanonaenyl)-, (all-E)-
InChi Key
FKUYMLZIRPABFK-IQSNHBBHSA-N
InChi Code
InChI=1S/C53H80O2/c1-40(2)21-13-22-41(3)23-14-24-42(4)25-15-26-43(5)27-16-28-44(6)29-17-30-45(7)31-18-32-46(8)33-19-34-47(9)35-20-36-48(10)37-38-51-39-52(54)49(11)50(12)53(51)55/h21,23,25,27,29,31,33,35,37,39H,13-20,22,24,26,28,30,32,34,36,38H2,1-12H3/b41-23+,42-25+,43-27+,44-29+,45-31+,46-33+,47-35+,48-37+
SMILES Code
O=C1C(C)=C(C)C(C(C/C=C(C)/CC/C=C(C)/CC/C=C(C)/CC/C=C(C)/CC/C=C(C)/CC/C=C(C)/CC/C=C(C)/CC/C=C(C)/CC/C=C(C)\C)=C1)=O
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

Preparing Stock Solutions

The following data is based on the product molecular weight 749.22 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
1: Szymańska R, Kruk J. Novel and rare prenyllipids - Occurrence and biological activity. Plant Physiol Biochem. 2018 Jan;122:1-9. doi: 10.1016/j.plaphy.2017.11.008. Epub 2017 Nov 14. Review. PubMed PMID: 29169080. 2: Zobnina V, Lambreva MD, Rea G, Campi G, Antonacci A, Scognamiglio V, Giardi MT, Polticelli F. The plastoquinol-plastoquinone exchange mechanism in photosystem II: insight from molecular dynamics simulations. Photosynth Res. 2017 Jan;131(1):15-30. Epub 2016 Jul 4. PubMed PMID: 27376842. 3: Silachev DN, Plotnikov EY, Zorova LD, Pevzner IB, Sumbatyan NV, Korshunova GA, Gulyaev MV, Pirogov YA, Skulachev VP, Zorov DB. Neuroprotective Effects of Mitochondria-Targeted Plastoquinone and Thymoquinone in a Rat Model of Brain Ischemia/Reperfusion Injury. Molecules. 2015 Aug 11;20(8):14487-503. doi: 10.3390/molecules200814487. PubMed PMID: 26270657; PubMed Central PMCID: PMC6332348. 4: Korshunova GA, Shishkina AV, Skulachev MV. Design, Synthesis, and Some Aspects of the Biological Activity of Mitochondria-Targeted Antioxidants. Biochemistry (Mosc). 2017 Jul;82(7):760-777. doi: 10.1134/S0006297917070021. Review. PubMed PMID: 28918741. 5: Røkke G, Melø TB, Hohmann-Marriott MF. The plastoquinone pool of Nannochloropsis oceanica is not completely reduced during bright light pulses. PLoS One. 2017 Apr 12;12(4):e0175184. doi: 10.1371/journal.pone.0175184. eCollection 2017. PubMed PMID: 28403199; PubMed Central PMCID: PMC5389811. 6: Tanaka K, Kaneko M, Ishikawa M, Kato S, Ito H, Kamachi T, Kamiya K, Nakanishi S. Specific Interaction between Redox Phospholipid Polymers and Plastoquinone in Photosynthetic Electron Transport Chain. Chemphyschem. 2017 Apr 19;18(8):878-881. doi: 10.1002/cphc.201700065. Epub 2017 Feb 23. PubMed PMID: 28194920. 7: Ksas B, Becuwe N, Chevalier A, Havaux M. Plant tolerance to excess light energy and photooxidative damage relies on plastoquinone biosynthesis. Sci Rep. 2015 Jun 3;5:10919. doi: 10.1038/srep10919. PubMed PMID: 26039552; PubMed Central PMCID: PMC4454199. 8: Lambreva MD, Russo D, Polticelli F, Scognamiglio V, Antonacci A, Zobnina V, Campi G, Rea G. Structure/function/dynamics of photosystem II plastoquinone binding sites. Curr Protein Pept Sci. 2014;15(4):285-95. Review. PubMed PMID: 24678671; PubMed Central PMCID: PMC4030317. 9: Van Eerden FJ, Melo MN, Frederix PWJM, Periole X, Marrink SJ. Exchange pathways of plastoquinone and plastoquinol in the photosystem II complex. Nat Commun. 2017 May 10;8:15214. doi: 10.1038/ncomms15214. PubMed PMID: 28489071; PubMed Central PMCID: PMC5436218. 10: Zernii EY, Gancharova OS, Baksheeva VE, Golovastova MO, Kabanova EI, Savchenko MS, Tiulina VV, Sotnikova LF, Zamyatnin AA Jr, Philippov PP, Senin II. Mitochondria-Targeted Antioxidant SkQ1 Prevents Anesthesia-Induced Dry Eye Syndrome. Oxid Med Cell Longev. 2017;2017:9281519. doi: 10.1155/2017/9281519. Epub 2017 Oct 12. PubMed PMID: 29158874; PubMed Central PMCID: PMC5660788. 11: Hasegawa R, Saito K, Takaoka T, Ishikita H. pK (a) of ubiquinone, menaquinone, phylloquinone, plastoquinone, and rhodoquinone in aqueous solution. Photosynth Res. 2017 Sep;133(1-3):297-304. doi: 10.1007/s11120-017-0382-y. Epub 2017 Apr 12. PubMed PMID: 28405861; PubMed Central PMCID: PMC5500672. 12: Skulachev MV, Skulachev VP. Programmed Aging of Mammals: Proof of Concept and Prospects of Biochemical Approaches for Anti-aging Therapy. Biochemistry (Mosc). 2017 Dec;82(12):1403-1422. doi: 10.1134/S000629791712001X. Review. PubMed PMID: 29486692. 13: Borisova-Mubarakshina MM, Vetoshkina DV, Ivanov BN. Antioxidant and signaling functions of the plastoquinone pool in higher plants. Physiol Plant. 2019 May;166(1):181-198. doi: 10.1111/ppl.12936. Epub 2019 Mar 6. Review. PubMed PMID: 30706486. 14: Kishi S, Saito K, Kato Y, Ishikita H. Redox potentials of ubiquinone, menaquinone, phylloquinone, and plastoquinone in aqueous solution. Photosynth Res. 2017 Nov;134(2):193-200. doi: 10.1007/s11120-017-0433-4. Epub 2017 Aug 22. PubMed PMID: 28831654; PubMed Central PMCID: PMC5645442. 15: Dilley RA. Frederick Loring Crane (1925-2016): Discoverer of coenzyme Q10 and rediscoverer of plastoquinone. Photosynth Res. 2017 Mar;131(3):237-239. doi: 10.1007/s11120-016-0319-x. Epub 2016 Nov 4. PubMed PMID: 27815800. 16: Sadre R, Frentzen M, Saeed M, Hawkes T. Catalytic reactions of the homogentisate prenyl transferase involved in plastoquinone-9 biosynthesis. J Biol Chem. 2010 Jun 11;285(24):18191-8. doi: 10.1074/jbc.M110.117929. Epub 2010 Apr 16. PubMed PMID: 20400515; PubMed Central PMCID: PMC2881743. 17: Tsybul'ko E, Krementsova A, Symonenko A, Rybina O, Roshina N, Pasyukova E. The Mitochondria-Targeted Plastoquinone-Derivative SkQ1 Promotes Health and Increases Drosophila melanogaster Longevity in Various Environments. J Gerontol A Biol Sci Med Sci. 2017 Apr 1;72(4):499-508. doi: 10.1093/gerona/glw084. PubMed PMID: 27166099; PubMed Central PMCID: PMC5861911. 18: Nowicka B, Żądło A, Pluciński B, Kruk J, Kuczyńska P. The oxidative stress in allelopathy: Participation of prenyllipid antioxidants in the response to juglone in Chlamydomonas reinhardtii. Phytochemistry. 2017 Dec;144:171-179. doi: 10.1016/j.phytochem.2017.09.012. Epub 2017 Sep 22. PubMed PMID: 28942064. 19: Silachev DN, Plotnikov EY, Pevzner IB, Zorova LD, Balakireva AV, Gulyaev MV, Pirogov YA, Skulachev VP, Zorov DB. Neuroprotective Effects of Mitochondria-Targeted Plastoquinone in a Rat Model of Neonatal Hypoxic⁻Ischemic Brain Injury. Molecules. 2018 Jul 27;23(8). pii: E1871. doi: 10.3390/molecules23081871. PubMed PMID: 30060443; PubMed Central PMCID: PMC6222533. 20: Bakeeva LE. Age-Related Changes in Ultrastructure of Mitochondria. Effect of SkQ1. Biochemistry (Mosc). 2015 Dec;80(12):1582-8. doi: 10.1134/S0006297915120068. Review. PubMed PMID: 26638683.