6-Shogaol supplier | CasNO.555-66-8

Name
6-Shogaol
EINECS
CAS No. 555-66-8
Article Data18
CAS DataBase
Density 1.033 g/cm³
Solubility
Melting Point
Formula C₁₇H₂₄O₃
Boiling Point 427.5 °C at 760 mmHg
Molecular Weight 276.376
Flash Point 150.3 °C
Transport Information
Appearance
Safety
Risk Codes 22
Molecular Structure
Hazard Symbols Xn
Synonyms Shogaol;[6]-Shogaol;
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%

: 555-66-8
[6]-shogaol

: 5538-51-2
O-acetylsalicyloyl chloride

: 6-shogaol aspirinate

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 0℃; for 2h;	93%

: 67-56-1
methanol

: 555-66-8
[6]-shogaol

: 5-methoxy-1-(4'-hydroxy-3'-methoxyphenyl)decan-3-one

Conditions

Conditions	Yield
With sodium methylate at 0℃; for 4h; Michael Addition;	90%

: 616-91-1
N-acetylcystein

: 555-66-8
[6]-shogaol

: 5-N-acetylcysteinyl-[6]-shogaol

Conditions

Conditions	Yield
With sodium hydrogencarbonate In methanol; water at 20℃; for 72h; Reagent/catalyst; Solvent; Temperature; Michael Addition;	80%

: 70-18-8
GLUTATHIONE

: 555-66-8
[6]-shogaol

: 5-glutathiol-[6]-shogaol

Conditions

Conditions	Yield
With sodium hydrogencarbonate In methanol; water at 20℃; for 3h; Michael Addition;	80%

: 555-66-8
[6]-shogaol

: 65-71-4
thymin

: 1-(1-(4-hydroxy-3-methoxyphenyl)-3-oxodecan-5-yl)-5-methylpyrimidine-2,4-(1H,3H)-dione

Conditions

Conditions	Yield
With triethylamine In dimethyl sulfoxide at 20℃; for 24h; Michael Addition;	67%

: 555-66-8
[6]-shogaol

: (1E,4E)-1-(4'-hydroxy-3'-methoxyphenyl)-deca-1,4-dien-3-one

Conditions

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In tetrahydrofuran at 0 - 20℃; for 3.5h;	62%

: 52-90-4
L-Cysteine

: 555-66-8
[6]-shogaol

: 5-cysteinyl-[6]-shogaol

Conditions

Conditions	Yield
With sodium hydrogencarbonate In methanol; water at 20℃; for 24h; Michael Addition;	60%

: 555-66-8
[6]-shogaol

: 5188-07-8
sodium thiomethoxide

: 5-methylthio-1-(4'-hydroxy-3'-methoxyphenyl)decan-3-one

Conditions

Conditions	Yield
In tetrahydrofuran; water at 20℃; for 6h; Michael Addition;	60%

: 1603-40-3
3-methylpyridin-2-ylamine

: 555-66-8
[6]-shogaol

: 1-(4-hydroxy-3-methoxyphenyl)-5-(3-methylpyridin-2-ylamino)decan-3-one

Conditions

Conditions	Yield
With triethylamine In dimethyl sulfoxide at 20℃; for 24h; Michael Addition;	57%

: 695-34-1
2-Amino-4-methylpyridine

: 555-66-8
[6]-shogaol

: 1-(4-hydroxy-3-methoxyphenyl)-5-(4-methylpyridin-2-ylamino)decan-3-one

Conditions

Conditions	Yield
With triethylamine In dimethyl sulfoxide at 20℃; for 24h; Michael Addition;	54%

: 1603-41-4
(5-methyl-pyridin-2-yl)amine

: 555-66-8
[6]-shogaol

: 1-(4-hydroxy-3-methoxyphenyl)-5-(5-methylpyridin-2-ylamino)decan-3-one

Conditions

Conditions	Yield
With triethylamine In dimethyl sulfoxide at 20℃; for 24h; Michael Addition;	50%

: 572-09-8, 3068-32-4, 4026-32-8, 6919-96-6, 13242-53-0, 14227-54-4, 14795-18-7, 19186-59-5, 19285-38-2, 21698-13-5, 29907-26-4, 53369-42-9, 60619-58-1, 61303-35-3, 67337-79-5, 69127-37-3, 70749-15-4, 72002-90-5, 75247-30-2, 75880-74-9, 78418-57-2, 102339-89-9, 102339-90-2, 103530-40-1, 114028-03-4, 114718-45-5, 138514-70-2, 138514-71-3
2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide

: 555-66-8
[6]-shogaol

: 4′-O-β-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-6-shogaol

Conditions

Conditions	Yield
With benzyltri(n-butyl)ammonium chloride; potassium hydroxide In chloroform; water at 20℃; for 6.5h;	44%

: 51-20-7
5-bromouracil

: 555-66-8
[6]-shogaol

: 5-bromo-1-(1-(4-hydroxy-3-methoxyphenyl)-3-oxodecan-5-yl)-pyrimidine-2,4-(1H,3H)-dione

Conditions

Conditions	Yield
With triethylamine In dimethyl sulfoxide at 20℃; for 24h; Michael Addition;	43%

: 555-66-8
[6]-shogaol

: 66224-66-6, 66224-67-7, 66224-68-8, 66224-69-9, 134434-48-3, 134434-49-4, 134454-76-5, 134461-75-9
adenine

: 1311378-31-0
5-(6-amino-9H-purin-9-yl)-1-(4-hydroxy-3-methoxyphenyl)decan-3-one

Conditions

Conditions	Yield
With triethylamine In dimethyl sulfoxide at 20℃; for 24h; Michael Addition;	38%
With caesium carbonate In methanol; water at 20℃; for 72h; Michael-type reaction;	36%

: 60-29-7
diethyl ether

: 555-66-8
[6]-shogaol

platinum black: platinum black

dihydroshogaol: dihydroshogaol

Conditions

Conditions	Yield
Hydrogenation;

...Expand

: 555-66-8
[6]-shogaol

: 2-methoxy-4-(5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-oxodecyl)phenyl methanesulfonate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / dimethyl sulfoxide / 24 h / 20 °C 2: triethylamine / dichloromethane / 2 h / 0 - 20 °C View Scheme

: 555-66-8
[6]-shogaol

: 2-methoxy-4-(5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-oxodecyl)phenyl 4-methylbenzenesulfonate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / dimethyl sulfoxide / 24 h / 20 °C 2: triethylamine / dichloromethane / 2 h / 0 - 20 °C View Scheme

: 555-66-8
[6]-shogaol

: 2-methoxy-4-(5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-oxodecyl)phenyl 6-chloronicotinate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / dimethyl sulfoxide / 24 h / 20 °C 2: triethylamine / dichloromethane / 2 h / 0 - 20 °C View Scheme

: 555-66-8
[6]-shogaol

: C38H42N2O9

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / dimethyl sulfoxide / 24 h / 20 °C 2: triethylamine / dichloromethane / 2 h / 0 - 20 °C View Scheme

: 555-66-8
[6]-shogaol

: 4-(5-(3-(furan-2-carbonyl)-5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-3-oxodecyl)-2-methoxyphenyl furan-2-carboxylate

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / dimethyl sulfoxide / 24 h / 20 °C 2: triethylamine / dichloromethane / 2 h / 0 - 20 °C View Scheme

6-Shogaol 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.

Product Name

6-Shogaol

Synthetic route

6-Shogaol Specification

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