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80154-34-3

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80154-34-3 Usage

Brief description

Helicid is the active ingredient isolated from the fruit of proteaceae plant Helicia nilagirica, with its chemical structure being similar to gastrodin (hydroxymethyl benzene - O-β-D-glucopyranoside). Pharmacological and clinical studies have shown that helicid has similar effects on the central nervous system with gastrodin, but its sedative, euthanasia and analgesic effect is stronger than gastrodin. The efficacy on the treatment of neurosis efficacy is definite without rebound insomnia and drug dependence. Therefore, it has excellent clinical value. Its fruit tablets have been used in clinical.

Extraction and Separation

Figure 1 the process of purification of helicid from the fruit of proteaceae plant Helicia nilagirica

Determination of content

HPLC method (1) Chromatographic conditions Column: YWCT-C18 (25cm × 2.6mm, 10μm) high pressure grouting method. Flowing phase: methanol-water (20:80); flow rate: 0.7 ml / min; column temperature: room temperature; UV detection wavelength: 270 nm; paper speed: 2.5 mm / min. (2) Reference solution preparation Precisely weigh control reference substance of helicid; prepare 1 mg/mL solution using 20% methanol. Precise weigh Bergenin; dissolve in 20% methanol; apply ultrasonic solubilization, dub bergenin into about 2mg / ml internal standard solution. (3) Preparation of sample solution Accurately weighed dried helicid powder of about 1g, and put it into 25ml volumetric flask; add 20 mL methanol for soak of 0.5 h; ultrasonic extraction 80min, cool, set volume into 25 mL with methanol; filter and filtrate will become the sample solution. (4) Determination Take helicid reference solution in 5ml volumetric flask, add bergenin internal standard solution of 1.5ml; diluted with 20% methanol to the mark, mix; take 5 mL sample solution, volatilize; add 1. 5mL the internal standard solution; dilute with 20% methanol to the mark, mix well. Take 5μl of both reference substance and sample solution, inject, determine according to the chromatographic conditions; calculate the content with peak area ratio. (5) Measurement results Use the above internal standard method to measure the content of helicid in Samples I and II, and the results were 0.963% and 0.928%. Its chemical structure is similar to Gastrodia; have a strong analgesic, sedation and euthanasia effect. It is used for the treatment of neurasthenia, neurasthenic syndrome, functional disorders, vascular headache and trigeminal neuralgia. It has remarkable effect on neurasthenic headache, dizziness and sleep disorders.

Chemical Properties

It appears as white needle-like crystals, mp.190 °C ~ 193 °C, [α] D20-100 ° ~ -108 ° (water).

Uses

It is used in the treatment of ischemic cardiovascular and cerebrovascular diseases. Also used in Chinese medicine in the treatment of headache and insomnia.

Check Digit Verification of cas no

The CAS Registry Mumber 80154-34-3 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 8,0,1,5 and 4 respectively; the second part has 2 digits, 3 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 80154-34:
(7*8)+(6*0)+(5*1)+(4*5)+(3*4)+(2*3)+(1*4)=103
103 % 10 = 3
So 80154-34-3 is a valid CAS Registry Number.
InChI:InChI=1/C13H16O7/c14-5-7-1-3-8(4-2-7)19-13-12(18)11(17)10(16)9(6-15)20-13/h1-5,9-13,15-18H,6H2/t9-,10-,11+,12-,13-/m1/s1

80154-34-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name Helicid

1.2 Other means of identification

Product number -
Other names 2-formylphenyl beta-L-glucopyranoside

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:80154-34-3 SDS

80154-34-3Synthetic route

C13H16O7*C5H9NO2

C13H16O7*C5H9NO2

formaldehydephenlyl-O-β-D-pyranosyl alloside
80154-34-3

formaldehydephenlyl-O-β-D-pyranosyl alloside

Conditions
ConditionsYield
In tetrahydrofuran at 50℃; for 24h;
β-D-allose pentaacetate
4257-94-7

β-D-allose pentaacetate

formaldehydephenlyl-O-β-D-pyranosyl alloside
80154-34-3

formaldehydephenlyl-O-β-D-pyranosyl alloside

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: triethylamine; boron trifluoride diethyl etherate / dichloromethane / 10 h / 0 - 50 °C
2: sodium methylate; methanol / 5 h / 80 °C
View Scheme
4-formylphenyl (2,3,4,6-tetra-O-acetyl)-β-D-allopyranoside
936574-32-2

4-formylphenyl (2,3,4,6-tetra-O-acetyl)-β-D-allopyranoside

formaldehydephenlyl-O-β-D-pyranosyl alloside
80154-34-3

formaldehydephenlyl-O-β-D-pyranosyl alloside

Conditions
ConditionsYield
With methanol; sodium methylate at 80℃; for 5h;
acetic anhydride
108-24-7

acetic anhydride

formaldehydephenlyl-O-β-D-pyranosyl alloside
80154-34-3

formaldehydephenlyl-O-β-D-pyranosyl alloside

4-formylphenyl (2,3,4,6-tetra-O-acetyl)-β-D-allopyranoside
936574-32-2

4-formylphenyl (2,3,4,6-tetra-O-acetyl)-β-D-allopyranoside

Conditions
ConditionsYield
With triethylamine In N,N-dimethyl-formamide at 0 - 20℃; for 14h;96%
With triethylamine In N,N-dimethyl-formamide at 20℃; for 2h; Cooling with ice;96%
With triethylamine In N,N-dimethyl-formamide at 20℃; Cooling with ice;94%
BARBITURIC ACID
67-52-7

BARBITURIC ACID

formaldehydephenlyl-O-β-D-pyranosyl alloside
80154-34-3

formaldehydephenlyl-O-β-D-pyranosyl alloside

5-[4-(β-D-allopyranosyloxy)benzylidene]-barbituric acid
950768-57-7

5-[4-(β-D-allopyranosyloxy)benzylidene]-barbituric acid

Conditions
ConditionsYield
In ethanol at 80℃; for 2h;95%
1-(4-fluorophenyl)ethanone
403-42-9

1-(4-fluorophenyl)ethanone

formaldehydephenlyl-O-β-D-pyranosyl alloside
80154-34-3

formaldehydephenlyl-O-β-D-pyranosyl alloside

(E)-3-(4-β-D-allopyranosyloxyphenyl)-1-(4-fluorophenyl)-propenone
1089671-19-1

(E)-3-(4-β-D-allopyranosyloxyphenyl)-1-(4-fluorophenyl)-propenone

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water Cooling with ice;86%
With sodium hydroxide In ethanol; water Claisen Schmidt condensation; Cooling with ice;65%
ethyl acetoacetate
141-97-9

ethyl acetoacetate

formaldehydephenlyl-O-β-D-pyranosyl alloside
80154-34-3

formaldehydephenlyl-O-β-D-pyranosyl alloside

2,6-dimethyl-3,5-dicarboethoxy-4-(4-β-D-allopyranosyloxyphenyl)-1,4-dihydropyridine
1320347-09-8

2,6-dimethyl-3,5-dicarboethoxy-4-(4-β-D-allopyranosyloxyphenyl)-1,4-dihydropyridine

Conditions
ConditionsYield
With ammonium acetate at 80℃; for 4.5h; Hantzsch reaction;82%
formaldehydephenlyl-O-β-D-pyranosyl alloside
80154-34-3

formaldehydephenlyl-O-β-D-pyranosyl alloside

acetylacetone
123-54-6

acetylacetone

2,6-dimethyl-3,5-dicarbomethyl-4-(4-β-D-allopyranosyloxyphenyl)-1,4-dihydropyridine
1320347-10-1

2,6-dimethyl-3,5-dicarbomethyl-4-(4-β-D-allopyranosyloxyphenyl)-1,4-dihydropyridine

Conditions
ConditionsYield
With ammonium acetate at 80℃; for 4.5h; Hantzsch reaction;82%
4,6-dihydroxy-2-mercaptopyrimidine
504-17-6

4,6-dihydroxy-2-mercaptopyrimidine

formaldehydephenlyl-O-β-D-pyranosyl alloside
80154-34-3

formaldehydephenlyl-O-β-D-pyranosyl alloside

5-[4-(β-D-allopyranosyloxy)benzylidene]-2-thiobarbituric acid
950768-59-9

5-[4-(β-D-allopyranosyloxy)benzylidene]-2-thiobarbituric acid

Conditions
ConditionsYield
In ethanol at 80℃; for 2h;81%
1,3-cylohexanedione
504-02-9

1,3-cylohexanedione

acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

formaldehydephenlyl-O-β-D-pyranosyl alloside
80154-34-3

formaldehydephenlyl-O-β-D-pyranosyl alloside

2-methyl-3-carbomethoxy-4-(4-β-D-allopyranosyloxyphenyl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline
1320347-13-4

2-methyl-3-carbomethoxy-4-(4-β-D-allopyranosyloxyphenyl)-5-oxo-1,4,5,6,7,8-hexahydroquinoline

Conditions
ConditionsYield
With ammonium acetate at 80℃; for 4h; Hantzsch reaction; Sonication;81%
acetoacetic acid methyl ester
105-45-3

acetoacetic acid methyl ester

formaldehydephenlyl-O-β-D-pyranosyl alloside
80154-34-3

formaldehydephenlyl-O-β-D-pyranosyl alloside

2,6-dimethyl-3,5-dicarbomethoxy-4-(4-β-D-allopyranosyloxyphenyl)-1,4-dihydropyridine
1320347-08-7

2,6-dimethyl-3,5-dicarbomethoxy-4-(4-β-D-allopyranosyloxyphenyl)-1,4-dihydropyridine

Conditions
ConditionsYield
With ammonium acetate at 80℃; for 4.5h; Hantzsch reaction;81%
formaldehydephenlyl-O-β-D-pyranosyl alloside
80154-34-3

formaldehydephenlyl-O-β-D-pyranosyl alloside

3'-Chloroacetophenone
99-02-5

3'-Chloroacetophenone

C21H21ClO7
1191907-65-9

C21H21ClO7

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water at 0℃; for 10h; Claisen Schmidt condensation;80%
formaldehydephenlyl-O-β-D-pyranosyl alloside
80154-34-3

formaldehydephenlyl-O-β-D-pyranosyl alloside

C28H32N2O7
953425-69-9

C28H32N2O7

Conditions
ConditionsYield
With triethylamine In ethanol at 60℃;78.7%
dimedone
126-81-8

dimedone

formaldehydephenlyl-O-β-D-pyranosyl alloside
80154-34-3

formaldehydephenlyl-O-β-D-pyranosyl alloside

9-(4-β-D-allopyranosyloxyphenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione
1320347-12-3

9-(4-β-D-allopyranosyloxyphenyl)-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydroacridine-1,8(2H,5H)-dione

Conditions
ConditionsYield
With ammonium acetate at 80℃; for 4.5h; Hantzsch reaction;78%
1,3-cylohexanedione
504-02-9

1,3-cylohexanedione

formaldehydephenlyl-O-β-D-pyranosyl alloside
80154-34-3

formaldehydephenlyl-O-β-D-pyranosyl alloside

9-(4-β-D-allopyranosyloxyphenyl)-3,4,6,7,9,10-hexahydroacridine-1,8 (2H,5H)-dione
1320347-11-2

9-(4-β-D-allopyranosyloxyphenyl)-3,4,6,7,9,10-hexahydroacridine-1,8 (2H,5H)-dione

Conditions
ConditionsYield
With ammonium acetate at 80℃; for 4.5h; Hantzsch reaction;76%
formaldehydephenlyl-O-β-D-pyranosyl alloside
80154-34-3

formaldehydephenlyl-O-β-D-pyranosyl alloside

p-toluenesulfonyl chloride
98-59-9

p-toluenesulfonyl chloride

4-formylphenyl 2,4-di-O-(4-toluenesulfonyl)-β-D-allopyranoside

4-formylphenyl 2,4-di-O-(4-toluenesulfonyl)-β-D-allopyranoside

Conditions
ConditionsYield
With 1-methyl-1H-imidazole; 2-((R)-quinolin-4-yl((1S,2R,4S,5R)-5-vinylquinuclidin-2-yl)methyl)-2,3-dihydro-1H-benzo[c][1,2]azaborol-1-ol; sodium carbonate In acetonitrile at 20℃; for 48h; regioselective reaction;74%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

formaldehydephenlyl-O-β-D-pyranosyl alloside
80154-34-3

formaldehydephenlyl-O-β-D-pyranosyl alloside

4-formylphenyl (4,6-O-benzylidene)-β-D-allopyranoside
1101836-70-7

4-formylphenyl (4,6-O-benzylidene)-β-D-allopyranoside

Conditions
ConditionsYield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 50℃; for 12h;70%
4-ethylacetophenone
937-30-4

4-ethylacetophenone

formaldehydephenlyl-O-β-D-pyranosyl alloside
80154-34-3

formaldehydephenlyl-O-β-D-pyranosyl alloside

E-(4-β-D-allopyranosyloxyphenyl)-1-(4-ethylphenyl)propenone
1089671-20-4

E-(4-β-D-allopyranosyloxyphenyl)-1-(4-ethylphenyl)propenone

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water Claisen Schmidt condensation; Cooling with ice;70%
benzyl bromide
100-39-0

benzyl bromide

formaldehydephenlyl-O-β-D-pyranosyl alloside
80154-34-3

formaldehydephenlyl-O-β-D-pyranosyl alloside

4-(((2S,3R,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)benzaldehyde

4-(((2S,3R,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)oxy)benzaldehyde

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 20℃; for 5h; Alkaline conditions; Cooling with ice;70%
trityl chloride
76-83-5

trityl chloride

formaldehydephenlyl-O-β-D-pyranosyl alloside
80154-34-3

formaldehydephenlyl-O-β-D-pyranosyl alloside

4-formylphenyl (6-O-triphenylmethyl)-β-D-allopyranoside
950761-93-0

4-formylphenyl (6-O-triphenylmethyl)-β-D-allopyranoside

Conditions
ConditionsYield
In pyridine at 20℃;68%
N-methoxylamine hydrochloride
593-56-6

N-methoxylamine hydrochloride

formaldehydephenlyl-O-β-D-pyranosyl alloside
80154-34-3

formaldehydephenlyl-O-β-D-pyranosyl alloside

C14H19NO7
950768-21-5

C14H19NO7

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water at 45℃; for 6h; pH=6 - 7;66%
formaldehydephenlyl-O-β-D-pyranosyl alloside
80154-34-3

formaldehydephenlyl-O-β-D-pyranosyl alloside

A

β-D-allopyranose
7283-09-2

β-D-allopyranose

B

4-hydroxy-benzaldehyde
123-08-0

4-hydroxy-benzaldehyde

Conditions
ConditionsYield
With sulfuric acid In water for 6h; structure explanation; hydrolysis, also with Emulsin;A 63%
B 32%
formaldehydephenlyl-O-β-D-pyranosyl alloside
80154-34-3

formaldehydephenlyl-O-β-D-pyranosyl alloside

acetone
67-64-1

acetone

4-formylphenyl (2,3-O-isopropylidene)-β-D-allopyranoside
950761-90-7

4-formylphenyl (2,3-O-isopropylidene)-β-D-allopyranoside

Conditions
ConditionsYield
With iodine at 20℃; for 3h;56%
thiosemicarbazide
79-19-6

thiosemicarbazide

formaldehydephenlyl-O-β-D-pyranosyl alloside
80154-34-3

formaldehydephenlyl-O-β-D-pyranosyl alloside

C14H19N3O6S
950768-20-4

C14H19N3O6S

Conditions
ConditionsYield
In ethanol Reflux;
formaldehydephenlyl-O-β-D-pyranosyl alloside
80154-34-3

formaldehydephenlyl-O-β-D-pyranosyl alloside

C13H17NO7
948990-95-2

C13H17NO7

Conditions
ConditionsYield
With hydroxylamine hydrochloride; sodium hydroxide In ethanol; water at 45℃; for 6h; pH=6 - 7;
para-chloroacetophenone
99-91-2

para-chloroacetophenone

formaldehydephenlyl-O-β-D-pyranosyl alloside
80154-34-3

formaldehydephenlyl-O-β-D-pyranosyl alloside

C21H21ClO7
1089663-30-8

C21H21ClO7

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water
para-bromoacetophenone
99-90-1

para-bromoacetophenone

formaldehydephenlyl-O-β-D-pyranosyl alloside
80154-34-3

formaldehydephenlyl-O-β-D-pyranosyl alloside

C21H21BrO7
1089663-31-9

C21H21BrO7

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water
formaldehydephenlyl-O-β-D-pyranosyl alloside
80154-34-3

formaldehydephenlyl-O-β-D-pyranosyl alloside

para-methylacetophenone
122-00-9

para-methylacetophenone

C22H24O7
1089663-27-3

C22H24O7

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water
para-chloroacetophenone
99-91-2

para-chloroacetophenone

formaldehydephenlyl-O-β-D-pyranosyl alloside
80154-34-3

formaldehydephenlyl-O-β-D-pyranosyl alloside

C21H21ClO7
949143-88-8

C21H21ClO7

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water Claisen Schmidt condensation;
para-bromoacetophenone
99-90-1

para-bromoacetophenone

formaldehydephenlyl-O-β-D-pyranosyl alloside
80154-34-3

formaldehydephenlyl-O-β-D-pyranosyl alloside

C21H21BrO7
949143-89-9

C21H21BrO7

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water Claisen Schmidt condensation;
formaldehydephenlyl-O-β-D-pyranosyl alloside
80154-34-3

formaldehydephenlyl-O-β-D-pyranosyl alloside

acetophenone
98-86-2

acetophenone

(E)-3-(4-β-D-allopyranosyloxyphenyl)-1-phenylpropenone
949143-84-4

(E)-3-(4-β-D-allopyranosyloxyphenyl)-1-phenylpropenone

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water Claisen Schmidt condensation;
With sodium hydroxide In ethanol; water
formaldehydephenlyl-O-β-D-pyranosyl alloside
80154-34-3

formaldehydephenlyl-O-β-D-pyranosyl alloside

para-methylacetophenone
122-00-9

para-methylacetophenone

C22H24O7
949143-85-5

C22H24O7

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water Claisen Schmidt condensation;
formaldehydephenlyl-O-β-D-pyranosyl alloside
80154-34-3

formaldehydephenlyl-O-β-D-pyranosyl alloside

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

C22H24O8
949143-87-7

C22H24O8

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water Claisen Schmidt condensation;

80154-34-3Relevant articles and documents

Preparation method of glucoside and derivatives thereof

-

Paragraph 0044-0045; 0048, (2020/04/02)

The invention discloses a preparation method of glucoside and derivatives thereof. According to the method, all hydroxyl groups on a sugar molecule structure are acetylated, a ligand containing phenolic hydroxyl groups is prepared at the same time, then boron trifluoride-diethyl ether is used as a catalyst, the two substances are condensed to obtain tetraacetylated glucoside, and finally acetyl protecting groups are removed to obtain the required glucoside. The method can selectively catalyze hemiacetal hydroxyl of monosaccharide to react with hydroxyl to obtain glucoside, and the product is single. The method is simple in production operation and low in equipment requirement, can be used for synthesizing glucoside and derivatives thereof with similar structures, is green and environment-friendly, and can be used for large-scale production.

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