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555-66-8

Basic Information
CAS No.: 555-66-8
Name: 4-Decen-3-one,1-(4-hydroxy-3-methoxyphenyl)-
Article Data: 18
Cas Database
Molecular Structure:
Molecular Structure of 555-66-8 (4-Decen-3-one,1-(4-hydroxy-3-methoxyphenyl)-)
Formula: C17H24O3
Molecular Weight: 276.376
Synonyms: Shogaol;[6]-Shogaol;
EINECS: N/A
Density: 1.033 g/cm3
Melting Point: N/A
Boiling Point: 427.5 °C at 760 mmHg
Flash Point: 150.3 °C
Solubility: N/A
Appearance: N/A
Hazard Symbols: Xn
Risk Codes: 22
Safety:
Transport Information: N/A
PSA: 46.53000
LogP: 4.03900
Synthetic route

ethyl 5-(4-hydroxy-3-methoxyphenyl)-3-oxopentanoate

66-25-1

hexanal

555-66-8

[6]-shogaol

Conditions
ConditionsYield
With sodium hydroxide In dimethyl sulfoxide at 0℃; for 0.5h;75%
Conditions
ConditionsYield
With potassium fluoride; C50H34F12O6 In toluene at 25℃; for 192h; Inert atmosphere; Resolution of racemate; enantioselective reaction;A n/a
B 48%
Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene Heating;
With potassium carbonate; methyl iodide In methanol at 20℃; for 48h;
66-25-1

hexanal

zingerone

zingerone

555-66-8

[6]-shogaol

Conditions
ConditionsYield
With potassium hydroxide; diethyl ether
1080-12-2

Dehydrozingerone

555-66-8

[6]-shogaol

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: H2 / Raney-Ni / -10 °C
2: (i) nBuLi, iPr2NH, THF, (ii) /BRN= 1209232/
3: TiCl4 / CH2Cl2 / -78 °C
4: TsOH / benzene / Heating
View Scheme
Multi-step reaction with 3 steps
1: sodium hydride / Reflux
2: hydrogen / acetone
3: sodium hydroxide / dimethyl sulfoxide / 0.5 h / 0 °C
View Scheme
122-48-5

4-(4-hydroxy-3-methoxyphenyl)-2-butanone

555-66-8

[6]-shogaol

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: (i) nBuLi, iPr2NH, THF, (ii) /BRN= 1209232/
2: TiCl4 / CH2Cl2 / -78 °C
3: TsOH / benzene / Heating
View Scheme
60101-00-0

2-Methoxy-1-trimethylsilanyloxy-4-(3-trimethylsilanyloxy-but-3-enyl)-benzene

555-66-8

[6]-shogaol

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: TiCl4 / CH2Cl2 / -78 °C
2: TsOH / benzene / Heating
View Scheme
121-33-5

vanillin

555-66-8

[6]-shogaol

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: BF3-Et2O / CH2Cl2
2: H2 / Raney-Ni / -10 °C
3: (i) nBuLi, iPr2NH, THF, (ii) /BRN= 1209232/
4: TiCl4 / CH2Cl2 / -78 °C
5: TsOH / benzene / Heating
View Scheme
555-66-8

[6]-shogaol

1-(4'-hydroxy-3'-methoxyphenyl)-4-decen-3-ol

Conditions
ConditionsYield
Stage #1: [6]-shogaol With cerium(III) chloride heptahydrate In methanol at -78℃; for 0.166667h;
Stage #2: With methanol; sodium tetrahydroborate at -78℃; for 0.5h;
100%
555-66-8

[6]-shogaol

27113-22-0

[6]-paradol

Conditions
ConditionsYield
With palladium 10% on activated carbon; hydrogen In tetrahydrofuran at 20℃;98%
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  • 6-shogaol CAS NO.555-66-8  CAS NO.555-66-8

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Specification

The 6-Shogaol, with the CAS registry number 555-66-8, is also known as (E)-1-(4-Hydroxy-3-methoxy-phenyl)dec-4-en-3-one. It belongs to the product categories of Miscellaneous Natural Products; The group of Ginerols. This chemical's molecular formula is C17H24O3 and molecular weight is 276.37. Its IUPAC name is called (E)-1-(4-hydroxy-3-methoxyphenyl)dec-4-en-3-one. This chemical's classification codes are Mutagens; Mutation data; Noxae.

Physical properties of 6-Shogaol: (1)ACD/LogP: 3.85; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 3.85; (4)ACD/LogD (pH 7.4): 3.85; (5)ACD/BCF (pH 5.5): 495.55; (6)ACD/BCF (pH 7.4): 494.36; (7)ACD/KOC (pH 5.5): 2956.26; (8)ACD/KOC (pH 7.4): 2949.15; (9)#H bond acceptors: 3; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 10; (12)Index of Refraction: 1.521; (13)Molar Refractivity: 81.51 cm3; (14)Molar Volume: 267.4 cm3; (15)Surface Tension: 38.4 dyne/cm; (16)Density: 1.033 g/cm3; (17)Flash Point: 150.3 °C; (18)Enthalpy of Vaporization: 70.89 kJ/mol; (19)Boiling Point: 427.5 °C at 760 mmHg; (20)Vapour Pressure: 6.55E-08 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)Canonical SMILES: CCCCCC=CC(=O)CCC1=CC(=C(C=C1)O)OC
(2)Isomeric SMILES: CCCCC/C=C/C(=O)CCC1=CC(=C(C=C1)O)OC
(3)InChI: InChI=1S/C17H24O3/c1-3-4-5-6-7-8-15(18)11-9-14-10-12-16(19)17(13-14)20-2/h7-8,10,12-13,19H,3-6,9,11H2,1-2H3/b8-7+
(4)InChIKey: OQWKEEOHDMUXEO-BQYQJAHWSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 109mg/kg (109mg/kg)   Journal of Pharmacobio-Dynamics. Vol. 7, Pg. 836, 1984.
mouse LD50 intravenous 50900ug/kg (50.9mg/kg)   Journal of Pharmacobio-Dynamics. Vol. 7, Pg. 836, 1984.
mouse LD50 oral 687mg/kg (687mg/kg)   Journal of Pharmacobio-Dynamics. Vol. 7, Pg. 836, 1984.