ubiquinone-9

Names

[ CAS No. ]:
303-97-9

[ Name ]:
ubiquinone-9

[Synonym ]:
ubiquinone-9
Ubidecarenone impurity D
Coenzyme Q9
Coenzyme Q9
Ubiquinone Q(sub 9)
CoQ(sub 9)
Coenzyme Q(sub 9)
2,3-dimethoxy-6-methyl-5-nonaisoprenoid-1,4-benzoquinone
2,3-Dimethoxy-5-methyl-6-[(2E,6E,10E,14E,18E,22E,26E,30E)-3,7,11,15,19,23,27,31,35-nonamethyl-2,6,10,14,18,22,26,30,34-hexatriacontanonaen-1-yl]-1,4-benzoquinone
All-Trans Coenzyme Q9
2,3-dimethoxy-5-methyl-2-<(all-E)-3',7',11',15',19',23',27',31',35'-nonamethylhexatriaconta-2',6',10',14',18',22',26',30',34',nonaenyl>cyclohexa-2,5-dien-1,4-dion
CoQ9
ubiquinone Q9
2,5-Cyclohexadiene-1,4-dione, 2,3-dimethoxy-5-methyl-6-[(2E,6E,10E,14E,18E,22E,26E,30E)-3,7,11,15,19,23,27,31,35-nonamethyl-2,6,10,14,18,22,26,30,34-hexatriacontanonaen-1-yl]-
2,3-dimethoxy-5-methyl-6-[(2E,6E,10E,14E,18E,22E,26E,30E)-3,7,11,15,19,23,27,31,35-nonamethylhexatriaconta-2,6,10,14,18,22,26,30,34-nonaenyl]cyclohexa-2,5-diene-1,4-dione
Ubidecarenone Related Compound A
Ubiquinone-45
Q-9 Ubiquinone-45 Ubiquinone-9

Biological Activity

[Description]:

Coenzyme Q9, a nine isoprenyl group-containing member of the ubiquinone family, is a normal constituent of human plasma.

[Related Catalog]:

Research Areas >> Cardiovascular Disease

Natural Products >> Quinones

[Target]

Human Endogenous Metabolite

[In Vitro]

Both CoQ9 and CoQ10 are equally cardioprotective, as evidenced by their abilities to improve left ventricular performance and to reduce myocardial infarct size and cardiomyocyte apoptosis. HPLC analysis reveals that a substantial portion of CoQ9 has been converted into CoQ10[1]. CoQ10 and CoQ9 are components of themitochondrial respiratory chain in mammals and can regulate some mitochondrial proteins/functions. Soybean, corn, and rapeseed oils are very rich sources of CoQ10, whereas CoQ9 has been found in high concentrations in corn oil[2].

[In Vivo]

The lack of a functional CoQ9 protein in homozygous CoQ9 mutant (CoQ9(X/X)) mice causes a severe reduction in the CoQ7 protein and a widespread CoQ deficiency and accumulation of demethoxyubiquinone. The deficit in CoQ induces a brain-specific impairment of mitochondrial bioenergetics performance, a reduction in respiratory control ratio, ATP levels and ATP/ADP ratio and specific loss of respiratory complex I. These effects lead to neuronal death and demyelinization with severe vacuolization and astrogliosis in the brain of CoQ9 (X/X) mice that consequently die between 3 and 6 months of age[3].

[References]

[1]. Lekli I, et al. Coenzyme Q9 provides cardioprotection after converting into coenzyme Q10. J Agric Food Chem. 2008 Jul 9;56(13):5331-7.

[2]. Venegas C, et al. Determination of coenzyme Q10, coenzyme Q9, and melatonin contents in virgin argan oils: comparison with other edible vegetable oils. J Agric Food Chem. 2011 Nov 23;59(22):12102-8.

[3]. García-Corzo L, et al. Dysfunctional Coq9 protein causes predominant encephalomyopathy associated with CoQ deficiency. Hum Mol Genet. 2013 Mar 15;22(6):1233-48.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
826.8±65.0 °C at 760 mmHg

[ Melting Point ]:
41-43ºC

[ Molecular Formula ]:
C₅₄H₈₂O₄

[ Molecular Weight ]:
795.227

[ Flash Point ]:
314.4±34.3 °C

[ Exact Mass ]:
794.621338

[ PSA ]:
52.60000

[ LogP ]:
18.89

[ Vapour Pressure ]:
0.0±3.0 mmHg at 25°C

[ Index of Refraction ]:
1.525

[ Storage condition ]:
-20°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DK4786000

CHEMICAL NAME :: p-Benzoquinone, 2,3-dimethoxy-5-methyl-6-(3,7,11,15,19,23,27,31,35-no namethyl-2,6,10,14,18, 22,26,30,34-hexatriacontanonaenyl)-

CAS REGISTRY NUMBER :: 303-97-9

BEILSTEIN REFERENCE NO. :: 1900081

LAST UPDATED :: 199612

DATA ITEMS CITED :: 9

MOLECULAR FORMULA :: C54-H82-O4

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >4 gm/kg

TOXIC EFFECTS :: 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: 3,147,1969

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >800 mg/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - ataxia 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: 3,147,1969

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >600 mg/kg

TOXIC EFFECTS :: 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: 3,147,1969

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >250 mg/kg

TOXIC EFFECTS :: 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: 3,147,1969

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >10 gm/kg

TOXIC EFFECTS :: 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: 3,147,1969

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 2 gm/kg

TOXIC EFFECTS :: Behavioral - ataxia 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: 3,147,1969

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >1500 mg/kg

TOXIC EFFECTS :: 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: 3,147,1969

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >500 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - ataxia

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 3,147,1969 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 11250 mg/kg/45D-C

TOXIC EFFECTS :: Gastrointestinal - other changes Liver - changes in liver weight Endocrine - changes in spleen weight

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 3,147,1969

Safety Information

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

[ Safety Phrases ]:
S22

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
DK4786000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

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