ubiquinone-9

Modify Date: 2024-01-03 14:06:36

ubiquinone-9 Structure
ubiquinone-9 structure
 Common Name ubiquinone-9
CAS Number 303-97-9 Molecular Weight 795.227
Density 1.0±0.1 g/cm3 Boiling Point 826.8±65.0 °C at 760 mmHg
Molecular Formula C54H82O4 Melting Point 41-43ºC
MSDS Chinese USA Flash Point 314.4±34.3 °C

 Use of ubiquinone-9


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

 Names

Name ubiquinone-9
Synonym More Synonyms

 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
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.

 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

 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

 Articles50

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 Synonyms

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
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