Product Name

  • Name

    Helicid

  • EINECS 1592732-453-0
  • CAS No. 80154-34-3
  • Article Data2
  • CAS DataBase
  • Density 1.51 g/cm3
  • Solubility Soluble in hot water. Slightly soluble in water, ethanol or carbinol. Insoluble in aether or chloroform.
  • Melting Point 199-200 °C
  • Formula C13H16O7
  • Boiling Point 559.9 °C at 760 mmHg
  • Molecular Weight 284.266
  • Flash Point 215.7 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 80154-34-3 (Helicid)
  • Hazard Symbols
  • Synonyms Helicide;Helicidum;
  • PSA 116.45000
  • LogP -1.32220

Synthetic 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%
...Expand
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%
natural Huperzine A
92138-20-0, 102518-79-6, 103735-86-0, 120786-18-7, 130791-77-4, 132435-40-6

natural Huperzine A

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;

Helicid Chemical Properties

Product Name: Benzaldehyde, 4-(b-D-allopyranosyloxy)- (CAS NO.80154-34-3)

Molecular Formula: C13H16O7
Molecular Weight: 284.26g/mol
Mol File: 80154-34-3.mol
Melting Point: 199-200°C
Index of Refraction: 1.65 
Molar Refractivity: 68.71 cm3 
Molar Volume: 188.1 cm3  
Surface Tension: 68.9 dyne/cm 
Density: 1.51 g/cm3 
Flash Point: 215.7 °C 
Enthalpy of Vaporization: 88.63 kJ/mol 
Boiling Point: 559.9 °C at 760 mmHg 
Vapour Pressure: 2.26E-13 mmHg at 25°C
XLogP3-AA: -0.9
H-Bond Donor: 4
H-Bond Acceptor: 7
Structure Descriptors of Benzaldehyde, 4-(b-D-allopyranosyloxy)- (CAS NO.80154-34-3):
  IUPAC Name: 4-[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxybenzaldehyde
  Canonical SMILES: C1=CC(=CC=C1C=O)OC2C(C(C(C(O2)CO)O)O)O
  InChI: InChI=1S/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 
  InChIKey: OLZAGZCCJJBKNZ-UHFFFAOYSA-N
Product Categories: Miscellaneous Natural Products; Allose; Biochemistry; Glycosides; Sugars; Natural Plant Extract

Helicid Specification

 Benzaldehyde, 4-(b-D-allopyranosyloxy)- , its CAS NO. is 80154-34-3, the synonyms are Helicid ; 4-(beta-D-allopyranosyloxy)-benzaldehyde .

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