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303-98-0

Basic Information
CAS No.: 303-98-0
Name: Ubidecarenone
Article Data: 53
Cas Database
Molecular Structure:
Molecular Structure of 303-98-0 (Ubidecarenone)
Formula: C59H90O4
Molecular Weight: 863.361
Synonyms: Terekol;Heartcin;Udekinon Emitolon;Ensorb;Ubiquinone 10;Ubiquinone 10 (Coenzyme Q10);Udekinon;Co Q10;CoQ10;Ubiquinone 50;Bio-Quinon;Q 199;Inokiten;Coenzyme Q10;Neuquinone;Q 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-;Water soluble coenzyme Q10;Ubidecarenone (Coenzyme Q10) USP28;CO-Q10;Coenzyme Q10(Ubiquinone);Ubidecarenone Coenzyme Q10;Ube-Q;Adelir;Coezime Q10;
EINECS: 206-147-9
Density: 0.97 g/cm3
Melting Point: 49-51 °C
Boiling Point: 869 °C at 760 mmHg
Flash Point: 324.5 °C
Solubility: N/A
Appearance: yellow-orange crystalline powder
Hazard Symbols: IrritantXi
Risk Codes: 36/37/38
Safety: 22-24/25-26
Transport Information: N/A
PSA: 52.60000
LogP: 17.85390
Synthetic route

(1α,4α,4aβ,8aβ)-(all-E)-(3,7,11,15,19,23,27,31,35,39-Decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaenyl)-1,4,4a,8a-tetrahydro-6,7-dimethoxy-4a-methyl-1,4-methanonaphthalene-5,8-dione

303-98-0

ubidecarenone

Conditions
ConditionsYield
In toluene for 0.5h; Heating;100%
899809-10-0

2-hydroxy-3,4,5-trimethoxy-6-((2E)-decaprenyl)-toluene

303-98-0

ubidecarenone

Conditions
ConditionsYield
With iron(III) chloride In dichloromethane; acetonitrile at 0 - 5℃; for 0.5h; Product distribution / selectivity;100%
With iron(III) chloride In dichloromethane; water; acetonitrile at 0 - 5℃; for 0.5h; Product distribution / selectivity;100%
With iron(III) chloride In di-isopropyl ether; water; ethyl acetate at 0 - 5℃; for 0.5h; Product distribution / selectivity;95%
ubiquinone-10-containing raw material

ubiquinone-10-containing raw material

303-98-0

ubidecarenone

Conditions
ConditionsYield
In ethanol; hexane at 25℃; for 0.733333h; Purification / work up;99.8%
64634-91-9

1-[(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]-3,4-dimethoxy-2,5-bis(methoxymethoxy)-6-methylbenzene

303-98-0

ubidecarenone

Conditions
ConditionsYield
With hydrogenchloride; iron(III) chloride In ethanol; hexane; water at 20℃; for 3h;95%
With hydrogenchloride; air In methanol; hexane at 40℃; for 4h;93%
With hydrogenchloride In methanol; hexane at 40℃; for 4h;93%
With air; hydrogen cation Yield given. Multistep reaction;
400010-26-6

2-((2E,6E,10E,14E,18E,22E,26E,30E,34E)-3,7,11,15,19,23,27,31,35,39-Decamethyl-tetraconta-2,6,10,14,18,22,26,30,34,38-decaenyl)-5,6-dimethoxy-3-methyl-phenol

303-98-0

ubidecarenone

Conditions
ConditionsYield
With salcomine; oxygen In N,N-dimethyl-formamide; toluene at 20℃; for 24h;94%
With pyridine; oxygen; sodium carbonate; salcomine In toluene; acetonitrile for 16h; Product distribution / selectivity;69%
303-98-0

ubidecarenone

Conditions
ConditionsYield
With sodium hydrogencarbonate at 50℃; pH=8; Temperature; pH-value;90.6%
With oxygen In ethanol for 24h; Conversion of starting material;46%
With oxygen; acetic acid In ethanol for 24h; Conversion of starting material;41%
75-24-1

trimethylaluminum

202843-56-9

2-chloromethyl-5,6-dimethoxy-3-methyl-[1,4]benzoquinone

400010-22-2

(all-E)-2,6,10,14,18,22,26,30,34-nonamethyl-2,6,10,14,18,22,26,30,34-nonacontanonaen-38-yne

303-98-0

ubidecarenone

Conditions
ConditionsYield
Stage #1: trimethylaluminum; (all-E)-2,6,10,14,18,22,26,30,34-nonamethyl-2,6,10,14,18,22,26,30,34-nonacontanonaen-38-yne With zirconocene dichloride In 1,2-dichloro-ethane at 23℃; for 1h;
Stage #2: 2-chloromethyl-5,6-dimethoxy-3-methyl-[1,4]benzoquinone With n-butyllithium; Cl2Ni(PPh)2; triphenylphosphine In tetrahydrofuran at 23℃; for 1h; Further stages.;
90%
Stage #1: trimethylaluminum; (all-E)-2,6,10,14,18,22,26,30,34-nonamethyl-2,6,10,14,18,22,26,30,34-nonacontanonaen-38-yne; zirconocene dichloride In dichloromethane; chlorobenzene at -15 - 0℃;
Stage #2: 2-chloromethyl-5,6-dimethoxy-3-methyl-[1,4]benzoquinone With bis(triphenylphosphine)nickel(II) chloride; n-butyllithium In tetrahydrofuran at -20℃; for 2h; Further stages.;
89%
Stage #1: trimethylaluminum; (all-E)-2,6,10,14,18,22,26,30,34-nonamethyl-2,6,10,14,18,22,26,30,34-nonacontanonaen-38-yne With methylalumoxane; rac-ethylenebis(1-indenyl)zirconium(IV) chloride In toluene at 20℃; for 22h; Negishi carboalumination;
Stage #2: 2-chloromethyl-5,6-dimethoxy-3-methyl-[1,4]benzoquinone; bis(triphenylphosphine)nickel(II) chloride; n-butyllithium In tetrahydrofuran at -20℃; for 2h;
88%

3,7,11,15,19,23,27,31,35,39-decamethyl-1-(3-isopropoxy-2-methyl-4,5,6-trimethoxyphenyl)tetraconta-2,6,10,14,18,22,26,30,34,38-decaene

303-98-0

ubidecarenone

Conditions
ConditionsYield
With ammonium cerium (IV) nitrate; nitric acid In tetrahydrofuran; water; acetonitrile at 0℃; for 0.5h;79%
70854-63-6

1,4-bis(benzyloxy)-2-{(2E,6E,10E,14E,18E,22E,26E,30E,34E)-3,7,11,15,19,23,27,31,35,39-decamethyl-5-[(4-methylphenyl)sulfonyl]tetraconta-2,6,10,14,18,22,26,30,34,38-decaenyl}-5,6-dimethoxy-3-methylbenzene

303-98-0

ubidecarenone

Conditions
ConditionsYield
With naphthalen-1-yl-lithium In tetrahydrofuran at -78℃; for 2h;77%
94828-17-8

(2'E,6'E,10'E,14'E,18'E,22'E,26'E,30'E,34'E,38'E)-1-(3',7',11',15',19',23',27',31',35',39'-decamethyltetraconta-2',6',10',14',18',22',26',30',34',38'-decaenyl)-6-methyl-2,3,4,5-tetramethoxybenzene

303-98-0

ubidecarenone

Conditions
ConditionsYield
With ceric ammoniumnitrate In dichloromethane; water; acetonitrile72%
With ammonium cerium(IV) nitrate In dichloromethane; acetonitrile at 0℃; for 0.5h;61%
With cerium(IV)diammonium nitrate; water In dichloromethane; acetonitrile at -5 - 3℃; for 1.28333h;
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History

In 1957, Ubidecarenone was first discovered by Professor Fredrick L. Crane and colleagues at the University of Wisconsin–Madison Enzyme Institute.  Its chemical structure was reported by Dr. Karl Folkers and coworkers at Merck in 1958; in 1968, Folkers became a Professor in the Chemistry Department at the University of Texas at Austin.

Consensus Reports

Reported in EPA TSCA Inventory.

Specification

Ubidecarenone, with the IUPAC Name of 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-decaenyl]-5,6-dimethoxy-3-methylcyclohexa-2,5-diene-1,4-dione, is one kind of fine powder. For being stable, it may be light or heat sensitive. Incompatible with strong oxidizing agents. It belongs to the Product Categories which include Drug bulk; Mixed Fatty Acids; Antioxidant; Benzoquinones; Biochemistry; Vitamin Related Compounds; Vitamins; Nutritional Supplements; Drugs & Medication; Fatty Acid Derivatives & Lipids; Glycerols; Steroids. Ubidecarenone can be widely used as antibacterial, antioxidant agent in food, cosmetics, dietary supplements industry.
 
Physical properties about Ubidecarenone are: (1)ACD/LogP: 19.119; (2)# of Rule of 5 Violations: 2; (3)ACD/LogD (pH 5.5): 19.12; (4)ACD/LogD (pH 7.4): 19.12; (5)ACD/BCF (pH 5.5): 1000000.00; (6)ACD/BCF (pH 7.4): 1000000.00; (7)ACD/KOC (pH 5.5): 10000000.00 ; (8)ACD/KOC (pH 7.4): 10000000.00; (9)#H bond acceptors: 4; (10)#Freely Rotating Bonds: 31; (11)Index of Refraction: 1.526; (12)Molar Refractivity: 272.647 cm3; (13)Molar Volume: 888.522 cm3 ; (14)Polarizability: 108.086 10-24cm3; (15)Surface Tension: 38.5900001525879 dyne/cm; (16)Density: 0.972 g/cm3; (17)Flash Point: 324.58 °C; (18)Enthalpy of Vaporization: 126.289 kJ/mol; (19)Boiling Point: 868.993 °C at 760 mmHg

You can still convert the following datas into molecular structure:
(1)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+;
(2)InChIKey=ACTIUHUUMQJHFO-UPTCCGCDSA-N;
(3)SmilesC(C(=C/CCC(=C/CCC(=C/CCC(=C/CCC(=C/CCC(=C/CCC(=C/CCC(=C/CCC(=C/CC1=C(C(C(=C(C1=O)OC)OC)=O)C)\C)\C)\C)\C)\C)\C)\C)\C)\C)C\C=C(/C)C

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD intramuscular > 500mg/kg (500mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Oyo Yakuri. Pharmacometrics. Vol. 6, Pg. 769, 1972.
mouse LD intravenous > 500mg/kg (500mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
Oyo Yakuri. Pharmacometrics. Vol. 6, Pg. 769, 1972.
mouse LD oral > 4gm/kg (4000mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Oyo Yakuri. Pharmacometrics. Vol. 6, Pg. 769, 1972.
mouse LD subcutaneous > 500mg/kg (500mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Oyo Yakuri. Pharmacometrics. Vol. 6, Pg. 769, 1972.
rat LD intramuscular > 500mg/kg (500mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Oyo Yakuri. Pharmacometrics. Vol. 6, Pg. 769, 1972.
rat LD intravenous > 250mg/kg (250mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
Oyo Yakuri. Pharmacometrics. Vol. 6, Pg. 769, 1972.
rat LD oral > 4gm/kg (4000mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
Oyo Yakuri. Pharmacometrics. Vol. 6, Pg. 769, 1972.
rat LD subcutaneous > 500mg/kg (500mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)
Oyo Yakuri. Pharmacometrics. Vol. 6, Pg. 769, 1972.

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