CAS No.555-66-8,6-Shogaol Suppliers,MSDS download

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Basic Information

Molecular Structure:
CAS No.:	555-66-8
Name:	6-Shogaol
Article Data:	18

Formula:	C₁₇H₂₄O₃
Molecular Weight:	276.376
Synonyms:	Shogaol;[6]-Shogaol;
Density:	1.033 g/cm³
Boiling Point:	427.5 °C at 760 mmHg
Flash Point:	150.3 °C
Hazard Symbols:	Xn
Risk Codes:	22
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

Conditions	Yield
With sodium hydroxide In dimethyl sulfoxide at 0℃; for 0.5h;	75%

: 23513-14-6, 72749-01-0, 74027-33-1, 39886-76-5
(+/-)-[6]-gingerol

A: 555-66-8
[6]-shogaol

B: 39886-76-5, 72749-01-0, 74027-33-1, 23513-14-6
[6]-gingerol

Conditions

Conditions	Yield
With potassium fluoride; C50H34F12O6 In toluene at 25℃; for 192h; Inert atmosphere; Resolution of racemate; enantioselective reaction;	A n/a B 48%

: 23513-14-6, 72749-01-0, 74027-33-1, 39886-76-5
(+/-)-[6]-gingerol

: 555-66-8
[6]-shogaol

Conditions

Conditions	Yield
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

Conditions	Yield
With potassium hydroxide; diethyl ether

: 1080-12-2
Dehydrozingerone

: 555-66-8
[6]-shogaol

Conditions

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
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

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In tetrahydrofuran at 20℃;	98%

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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)	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.