coenzyme Q10

Names

[ CAS No. ]:
303-98-0

[ Name ]:
coenzyme Q10

[Synonym ]:
coenzyme Q-10
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
CoQ10
Ube-Q
Coenzyme Q
Ubiquinone 50
Coenzyme Q 10
Ubiquinone 10
2-[(2E,6E,10E,14E,18E,22E,26E,30E,34E)-3,7,11,15,19,23,27,31,35,39-Decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaen-1-yl]-5,6-dimethoxy-3-methyl-1,4-benzoquinone
Coenzyme Q10
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-methyl-1,4-benzoquinone
Ensorb
Liquid-Q
Coenzyme Q10
Carenone
ubiquinone
EINECS 206-147-9
2,5-Cyclohexadiene-1,4-dione, 2-[(2E,6E,10E,14E,18E,22E,26E,30E,34E)-3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaen-1-yl]-5,6-dimethoxy-3-methyl-
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-dien-1,4-dion
ubiquinone (50)
Coenz10
neuqinon
ubiquinone Q10
MFCD00042919
eiquinon
Q-Gel
ubidecarenone
Bio-Quinon
Ubiquinone-10
2,5-Cyclohexadiene-1,4-dione, 2-[(2E,6E,10E,14E,18E,22E,26E,30E,34E)-3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaenyl]-5,6-dimethoxy-3-methyl-
Coenzyme Q10,Q-10,Ubiquinone 50
Q-10
Kudesan
Q-10 Ubiquinone 50 Ubiquinone-10

Biological Activity

[Description]:

Coenzyme Q10 is an essential cofactor of the electron transport chain and a potent antioxidant agent.

[Related Catalog]:

Research Areas >> Cancer

Research Areas >> Inflammation/Immunology

Research Areas >> Metabolic Disease

Research Areas >> Neurological Disease

Natural Products >> Quinones

[Target]

Human Endogenous Metabolite

[In Vitro]

Coenzyme Q10 is an obligatory member of the respiratory chain in the mitochondria of all cells. Therefore, it is an essential ingredient in the formation of adenosine triphosphate (ATP), the source of energy in most cellular processes. Coenzyme Q10 is located in the mitochondria, lysosomes, and Golgi and plasma membranes, and provides an antioxidant action either by direct reaction with free radicals or by regeneration of tocopherol and ascorbate from their oxidised state[1]. Coenzyme Q10 is a popular dietary supplement because of its recognition by the public as an important nutrient in supporting human health. The rationale for the use of Coenzyme Q10 as a therapeutic agent in several cardiovascular and degenerative neurologic and neuromuscular diseases is based upon its fundamental role in mitochondrial function and cellular bioenergetics[2].

[In Vivo]

Because of its hydrophobicity and large molecular weight, absorption of dietary Coenzyme Q10 is slow and limited. In the case of dietary supplements, solubilized Coenzyme Q10 formulations show enhanced bioavailability. The Tmax is around 6 h, with an elimination half-life of about 33 h. The reference intervals for plasma Coenzyme Q10 range from 0.40 to 1.91 mM in healthy subjects. With Coenzyme Q10 supplements there is reasonable correlation between increase in plasma Coenzyme Q10 and ingested dose up to a certain point. Animal data show that Coenzyme Q10 in large doses is taken up by all tissues including heart and brain mitochondria[2]. In 12-month-old rats administration of coenzyme Q10 results in significant increases in cerebral cortex mitochondrial concentrations of coenzyme Q10. Oral administration of coenzyme Q10 markedly attenuates striatal lesions produced by systemic administration of 3-nitropropionic acid and significantly increases life span in a transgenic mouse model of familial amyotrophic lateral sclerosis[3].

[Animal admin]

Rats[3] The effects of oral administration of coenzyme Q10 on 3-NP-induced striatal lesions are examined in 300- to 350-g rats (n=5-10). Animals receive either rat chow supplemented with coenzyme Q10 at 200 mg/kg or unsupplemented rat chow. After 1 week they are treated with 3-NP at a dose of 10 mgykg i.p. twice a day until either a control or treated animal became symptomatic with hindlimb dystonia, and then sacrificed in pairs[3]. Mice[3] To determine whether coenzyme Q10 exerts neuroprotective effects in a transgenic mouse model of a human neurodegenerative disorder, coenzyme Q10 (200 mg/kg) is administered orally to 16 transgenic mice overexpressing a human CuyZn superoxide dismutase (SOD1) mutation, as compared with 13 animals that receive unsupplemented rat chow. The mice used are the G1 line, which expresses high levels of human SOD with the G93A mutation. Treatment is started at 50 days after birth. Treatment is continued until mice reach end-stage disease[3].

[References]

[1]. Yang YK, et al. Coenzyme Q10 treatment of cardiovascular disorders of ageing including heart failure, hypertension and endothelial dysfunction. Clin Chim Acta. 2015 Oct 23;450:83-9.

[2]. Bhagavan HN, et al. Coenzyme Q10: absorption, tissue uptake, metabolism and pharmacokinetics. Free Radic Res. 2006 May;40(5):445-53.

[3]. Matthews RT, et al. Coenzyme Q10 administration increases brain mitochondrial concentrations and exerts neuroprotective effects. Proc Natl Acad Sci U S A. 1998 Jul 21;95(15):8892-7.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
869.0±65.0 °C at 760 mmHg

[ Melting Point ]:
49-51 °C

[ Molecular Formula ]:
C₅₉H₉₀O₄

[ Molecular Weight ]:
863.344

[ Flash Point ]:
324.6±34.3 °C

[ Exact Mass ]:
862.683899

[ PSA ]:
52.60000

[ LogP ]:
20.93

[ Vapour Pressure ]:
0.0±3.3 mmHg at 25°C

[ Index of Refraction ]:
1.526

[ Storage condition ]:
−20°C

[ Stability ]:
Stable, but may be light or heat sensitive. Store in the dark at -20 C. Incompatible with strong oxidizing agents.

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DK3900000

CHEMICAL NAME :: p-Benzoquinone, 2-(3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,1 8,22,26,30,34,38- tetracontadecaenyl)-5,6-dimethoxy-3-methyl-

CAS REGISTRY NUMBER :: 303-98-0

LAST UPDATED :: 199803

DATA ITEMS CITED :: 15

MOLECULAR FORMULA :: C59-H90-O4

MOLECULAR WEIGHT :: 863.49

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >4 gm/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - somnolence (general depressed activity)

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 6,769,1972

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >500 mg/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - somnolence (general depressed activity)

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 6,769,1972

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >250 mg/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - dyspnea

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 6,769,1972

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >500 mg/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - somnolence (general depressed activity)

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 6,769,1972

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >4 gm/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - somnolence (general depressed activity)

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 6,769,1972

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >500 mg/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - somnolence (general depressed activity)

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 6,769,1972

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >500 mg/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - dyspnea

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 6,769,1972

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Intramuscular

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >500 mg/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - somnolence (general depressed activity)

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 6,769,1972 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1400 mg/kg/5W-C

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - other changes Gastrointestinal - hypermotility, diarrhea Related to Chronic Data - death

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 6,769,1972 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 42 mg/kg

SEX/DURATION :: female 9-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - musculoskeletal system Reproductive - Effects on Newborn - physical

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 3,306,1972

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 4200 mg/kg

SEX/DURATION :: female 9-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetal death Reproductive - Specific Developmental Abnormalities - other developmental abnormalities

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 3,306,1972

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 42 mg/kg

SEX/DURATION :: female 7-13 day(s) after conception

TOXIC EFFECTS :: Reproductive - Specific Developmental Abnormalities - musculoskeletal system Reproductive - Effects on Newborn - physical

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 3,306,1972

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 4200 mg/kg

SEX/DURATION :: female 7-13 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetal death

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 3,306,1972

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 420 mg/kg

SEX/DURATION :: female 7-13 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

REFERENCE :: IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 3,306,1972

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xi: Irritant;

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
22-24/25-26

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
DK3900000

[ HS Code ]:
2932999099

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2932999099

[ Summary ]:
2932999099. other heterocyclic compounds with oxygen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Promotion of growth by Coenzyme Q10 is linked to gene expression in C. elegans

Biochem. Biophys. Res. Commun. 452(4) , 920-7, (2014)

• We systematically examined the relation between Coenzyme Q (CoQ) and growth in C. elegans. • Novel molecular targets differentially expressed by endogenous (clk-1 mutants) or exogenous CoQ are provi...

A nuclear role for the respiratory enzyme CLK-1 in regulating mitochondrial stress responses and longevity.

Nat. Cell Biol. 17 , 782-92, (2015)

The coordinated regulation of mitochondrial and nuclear activities is essential for cellular respiration and its disruption leads to mitochondrial dysfunction, a hallmark of ageing. Mitochondria commu...

Rapid high performance liquid chromatography-high resolution mass spectrometry methodology for multiple prenol lipids analysis in zebrafish embryos.

J. Chromatogr. A. 1412 , 59-66, (2015)

The analysis of lipid molecules in living organism is an important step in deciphering metabolic pathways. Recently, the zebrafish has been adopted as a valuable animal model system to perform in vivo...