Coenzyme Q10

Coenzyme Q₁₀
Names
	Preferred IUPAC name 2-[(2E,6E,10E,14E,18E,22E,26E,30E,34E)-3,7,11,15,19,23,27,31,35,39-Decamethyltetraconta-2,6,10,14,18,22,26,30,34,38-decaen-1-yl]-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione
	Other names In general: Ubiquinone, coenzyme Q, CoQ, vitamin Q (misnomer: being not required it cannot be a vitamin); This form: ubidecarenone,; Q10, CoQ10 /ˌkoʊˌkjuːˈtɛn/
Identifiers
CAS Number	303-98-0 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:46245 ;
ChEMBL	ChEMBL454801 ;
ChemSpider	4445197 ;
ECHA InfoCard	100.005.590
KEGG	C11378;
PubChem CID	5281915;
UNII	EJ27X76M46 ;
CompTox Dashboard (EPA)	DTXSID6046054 ;
	InChI InChI=1S/C59H90O4/c1-44(2)24-15-25-45(3)26-16-27-46(4)28-17-29-47(5)30-18-31-48(6)32-19-33-49(7)34-20-35-50(8)36-21-37-51(9)38-22-39-52(10)40-23-41-53(11)42-43-55-54(12)56(60)58(62-13)59(63-14)57(55)61/h24,26,28,30,32,34,36,38,40,42H,15-23,25,27,29,31,33,35,37,39,41,43H2,1-14H3/b45-26+,46-28+,47-30+,48-32+,49-34+,50-36+,51-38+,52-40+,53-42+ Key: ACTIUHUUMQJHFO-UPTCCGCDSA-N ; InChI=1/C59H90O4/c1-44(2)24-15-25-45(3)26-16-27-46(4)28-17-29-47(5)30-18-31-48(6)32-19-33-49(7)34-20-35-50(8)36-21-37-51(9)38-22-39-52(10)40-23-41-53(11)42-43-55-54(12)56(60)58(62-13)59(63-14)57(55)61/h24,26,28,30,32,34,36,38,40,42H,15-23,25,27,29,31,33,35,37,39,41,43H2,1-14H3/b45-26+,46-28+,47-30+,48-32+,49-34+,50-36+,51-38+,52-40+,53-42+ Key: ACTIUHUUMQJHFO-UPTCCGCDBK;
	SMILES O=C1/C(=C(\C(=O)C(\OC)=C1\OC)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)CC\C=C(/C)C;
Properties
Chemical formula	C59H90O4
Molar mass	863.365 g·mol−1
Appearance	yellow or orange solid
Melting point	48–52 °C (118–126 °F; 321–325 K)
Solubility in water	insoluble
Pharmacology
ATC code	C01EB09 (WHO)
Related compounds
Related quinones	1,4-Benzoquinone; Plastoquinone; Ubiquinol
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

Coenzyme Q (CoQ /ˌkoʊkjuː/), also known as ubiquinone, is a naturally occurring biochemical cofactor (coenzyme) and an antioxidant produced by the human body. The human body mainly produces the form known as coenzyme Q₁₀ (CoQ₁₀, ubidecarenone), but other forms exist.^[1]^[2]^[3] CoQ is used by and found in many organisms, including animals and bacteria. As a result, it can also be obtained from dietary sources, such as meat, fish, seed oils, vegetables, and dietary supplements.^[1]^[2]

CoQ plays a role in mitochondrial oxidative phosphorylation, aiding in the production of adenosine triphosphate (ATP), which is involved in energy transfer within cells.^[1] The structure of CoQ₁₀ consists of a benzoquinone moiety and an isoprenoid side chain, with the "10" referring to the number of isoprenyl chemical subunits in its tail.^[4]^[5]^[6]

Although a ubiquitous molecule in human tissues, CoQ₁₀ is not a dietary nutrient and does not have a recommended intake level, and its use as a supplement is not approved in the United States for any health or anti-disease effect.^[1]^[2]

^ ^a ^b ^c ^d "Coenzyme Q10". Micronutrient Information Center, Linus Pauling Institute, Oregon State University. 2018. Archived from the original on 15 March 2024. Retrieved 13 April 2024.
^ ^a ^b ^c Sood B, Preeti Patel P, Keenaghan M (30 January 2024). "Coenzyme Q10". StatPearls, US National Library of Medicine. PMID 30285386. Archived from the original on 2 October 2023. Retrieved 17 April 2024.
^ "Coenzyme Q10". National Center for Complementary and Integrative Health, US National Institutes of Health. January 2019. Archived from the original on 4 April 2024. Retrieved 13 April 2024.
^ Mantle D, Lopez-Lluch G, Hargreaves IP (January 2023). "Coenzyme Q10 Metabolism: A Review of Unresolved Issues". International Journal of Molecular Sciences. 24 (3): 2585. doi:10.3390/ijms24032585. PMC 9916783. PMID 36768907. This article incorporates text from this source, which is available under the CC BY 4.0 license.
^ Kadian M, Sharma G, Pandita S, Sharma K, Shrivasatava K, Saini N, et al. (2022). "The Impact of Coenzyme Q10 on Neurodegeneration: A Comprehensive Review". Current Pharmacology Reports. 8: 1–19. doi:10.1007/s40495-021-00273-6.
^ Mantle D, Heaton RA, Hargreaves IP (May 2021). "Coenzyme Q10 and Immune Function: An Overview". Antioxidants. 10 (5): 759. doi:10.3390/antiox10050759. PMC 8150987. PMID 34064686. This article incorporates text from this source, which is available under the CC BY 4.0 license.

[lpi-1] "Coenzyme Q10". Micronutrient Information Center, Linus Pauling Institute, Oregon State University. 2018. Archived from the original on 15 March 2024. Retrieved 13 April 2024.

[sood-2] Sood B, Preeti Patel P, Keenaghan M (30 January 2024). "Coenzyme Q10". StatPearls, US National Library of Medicine. PMID 30285386. Archived from the original on 2 October 2023. Retrieved 17 April 2024.

[nccih-3] "Coenzyme Q10". National Center for Complementary and Integrative Health, US National Institutes of Health. January 2019. Archived from the original on 4 April 2024. Retrieved 13 April 2024.

[pmid36768907-4] Mantle D, Lopez-Lluch G, Hargreaves IP (January 2023). "Coenzyme Q10 Metabolism: A Review of Unresolved Issues". International Journal of Molecular Sciences. 24 (3): 2585. doi:10.3390/ijms24032585. PMC 9916783. PMID 36768907. This article incorporates text from this source, which is available under the CC BY 4.0 license.

[Kadian-2022-5] Kadian M, Sharma G, Pandita S, Sharma K, Shrivasatava K, Saini N, et al. (2022). "The Impact of Coenzyme Q10 on Neurodegeneration: A Comprehensive Review". Current Pharmacology Reports. 8: 1–19. doi:10.1007/s40495-021-00273-6.

[pmid34064686-6] Mantle D, Heaton RA, Hargreaves IP (May 2021). "Coenzyme Q10 and Immune Function: An Overview". Antioxidants. 10 (5): 759. doi:10.3390/antiox10050759. PMC 8150987. PMID 34064686. This article incorporates text from this source, which is available under the CC BY 4.0 license.

[1]

[2]

[3]

[4]

[5]

[6]