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CAS No.138-52-3 2-(Hydroxymethyl)phenyl-beta-D-glucopyranoside
Cas No: 138-52-3
No Data 1 Kilogram 100 Metric Ton/Month Guangdong Juda Chemical Industrial Co.,Limited Contact Supplier
D(-)-Salicin
Cas No: 138-52-3
No Data No Data No Data Cartoon Ingredients Co., Ltd Contact Supplier
D(-)-Salicin
Cas No: 138-52-3
USD $ 3.0-3.0 / Kilogram 1 Kilogram 1-100 Metric Ton/Month Dayang Chem (Hangzhou) Co.,Ltd. Contact Supplier
High purity Salicoside with high quality and best price cas:138-52-3
Cas No: 138-52-3
USD $ 15.0-40.0 / Kilogram 1 Kilogram 99999 Kilogram/Year Hangzhou Dingyan Chem Co., Ltd Contact Supplier
138-52-3 D(-)-Salicin
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D(-)-Salicin CAS NO.138-52-3
Cas No: 138-52-3
USD $ 2.0-2.0 / Gram 100 Gram 100 Metric Ton/Month Hebei yanxi chemical co.,LTD. Contact Supplier
Cosmetic Grade Natural White Willow Bark / Salix Alba Bark Extract Powder 10:1
Cas No: 138-52-3
USD $ 18.0-23.0 / Kilogram 1 Kilogram 100000 Kilogram/Year Xi'an Quanao Biotech Co., Ltd. Contact Supplier
Salicin
Cas No: 138-52-3
No Data No Data No Data Chemwill Asia Co., Ltd. Contact Supplier
High Quality 99% salicine 138-52-3 GMP manufacturer
Cas No: 138-52-3
USD $ 0.1-0.1 / Gram 1 Gram 100 Metric Ton/Year Xi'an Xszo Chem Co., Ltd. Contact Supplier
Factory Supply Salicin
Cas No: 138-52-3
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138-52-3 Usage

Uses

Standard substrate in evaluating enzyme Preparations contg b-glucosidase: Weidenhagen, Z. Ver. Zucker-Ind. 79, 591 (1929).

Uses

analgesic, antipyretic

Purification Methods

Crystallise D(-)-salicin from EtOAc, EtOH or water and sublime it at 190-195o/12mm. [Armour et al. J Chem Soc 412 1961, IR: Pearl & Darling J Org Chem 24 731 1959, Beilstein 17 III/IV 2986, 17/7 V 113.]

Description

D(-)-Salicin is a traditional medicine which has been known to exhibit anti-inflammation and other therapeutic activities, it can inhibit the LPS-induced inflammation in RAW264.7 cells and mouse models.

Definition

ChEBI: An aryl beta-D-glucoside that is the beta-D-glucoside of the phenolic hydroxy group of salicyl alcohol.

Uses

H1 antihistamine (nonsedating)

Chemical Properties

white crystals or powder
InChI:InChI=1/C13H18O7/c14-5-7-3-1-2-4-8(7)19-13-12(18)11(17)10(16)9(6-15)20-13/h1-4,9-18H,5-6H2/t9-,10-,11+,12-,13-/m0/s1

138-52-3 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
Alfa Aesar (A16524)  D-(-)-Salicin, 99%    138-52-3 5g 274.0CNY Detail
Alfa Aesar (A16524)  D-(-)-Salicin, 99%    138-52-3 25g 1024.0CNY Detail
Alfa Aesar (A16524)  D-(-)-Salicin, 99%    138-52-3 100g 3365.0CNY Detail
Sigma-Aldrich (79588)  D-(−)-Salicin  analytical standard 138-52-3 79588-100MG 1,406.34CNY Detail
Sigma-Aldrich (Y0000669)  Salicin  European Pharmacopoeia (EP) Reference Standard 138-52-3 Y0000669 1,880.19CNY Detail
Sigma (S0625)  D-(−)-Salicin  ≥99% (GC) 138-52-3 S0625-5G 398.97CNY Detail
Sigma (S0625)  D-(−)-Salicin  ≥99% (GC) 138-52-3 S0625-25G 1,382.94CNY Detail
Sigma (S0625)  D-(−)-Salicin  ≥99% (GC) 138-52-3 S0625-100G 4,633.20CNY Detail

138-52-3SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 10, 2017

Revision Date: Aug 10, 2017

1.Identification

1.1 GHS Product identifier

Product name salicin

1.2 Other means of identification

Product number -
Other names D-(?)-Salicin

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:138-52-3 SDS

138-52-3Synthetic route

2-(hydroxymethyl)phenyl-2-O-acetyl-β-D-glucopyranoside

2-(hydroxymethyl)phenyl-2-O-acetyl-β-D-glucopyranoside

D-(-)-salicin
138-52-3

D-(-)-salicin

Conditions
ConditionsYield
With sodium methylate In methanol at 20℃; for 2h;99%
2-(hydroxymethyl)phenyl-6-O-acetyl-β-D-glucopyranoside
19764-02-4

2-(hydroxymethyl)phenyl-6-O-acetyl-β-D-glucopyranoside

D-(-)-salicin
138-52-3

D-(-)-salicin

Conditions
ConditionsYield
With sodium methylate In methanol at 20℃; for 2h;99%
2-({[(1-hydroxy-6-oxocyclohex-2-en-1-yl)carbonyl]oxy}methyl)phenyl β-D-glucopyranoside 2-benzoate
29836-40-6

2-({[(1-hydroxy-6-oxocyclohex-2-en-1-yl)carbonyl]oxy}methyl)phenyl β-D-glucopyranoside 2-benzoate

D-(-)-salicin
138-52-3

D-(-)-salicin

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 7h;46%
D-Glucose
2280-44-6

D-Glucose

salicylic alcohol
90-01-7

salicylic alcohol

A

2-hydroxybenzyl alcohol-7-O-β-D-glucopyranoside
7724-09-6, 10367-12-1, 138128-00-4

2-hydroxybenzyl alcohol-7-O-β-D-glucopyranoside

B

D-(-)-salicin
138-52-3

D-(-)-salicin

Conditions
ConditionsYield
With almond β-D-glucosidase In water; acetonitrile at 40℃; for 48h; Enzymatic reaction;A 9%
B 6%
D-(-)-salicin
138-52-3

D-(-)-salicin

Conditions
ConditionsYield
With 1,4-dioxane; lithium aluminium tetrahydride; diethyl ether anschl. mit Methanol;
2-[[[(1-hydroxy-6-oxo-2-cyclohexen-1-yl)carbonyl]hydroxy]methyl]phenyl-β-D-glucopyranoside
29836-41-7

2-[[[(1-hydroxy-6-oxo-2-cyclohexen-1-yl)carbonyl]hydroxy]methyl]phenyl-β-D-glucopyranoside

A

2-hydroxy-2-cyclohexen-1-one
10316-66-2

2-hydroxy-2-cyclohexen-1-one

(+)-6-hydroxycyclohexen-2-one

(+)-6-hydroxycyclohexen-2-one

C

D-(-)-salicin
138-52-3

D-(-)-salicin

Conditions
ConditionsYield
enzyme from Populus balsamifera at 27℃; incubation;
pruyanaside A

pruyanaside A

A

virgaureoside A

virgaureoside A

B

D-(-)-salicin
138-52-3

D-(-)-salicin

C

o-methoxycarbonylphenyl β-D-glucopyranoside
10019-60-0

o-methoxycarbonylphenyl β-D-glucopyranoside

Conditions
ConditionsYield
With sodium methylate In methanol for 1h; Ambient temperature;
pruyanaside B

pruyanaside B

A

methyl 2-β-D-glucopyranosyloxy-6-hydroxybenzoate
108124-75-0

methyl 2-β-D-glucopyranosyloxy-6-hydroxybenzoate

B

populine

populine

C

henryoside

henryoside

D

D-(-)-salicin
138-52-3

D-(-)-salicin

Conditions
ConditionsYield
With sodium methylate In methanol for 1h; Ambient temperature;
2-methyl-benzyl alcohol
89-95-2

2-methyl-benzyl alcohol

Sucrose
57-50-1

Sucrose

A

2-hydroxybenzyl alcohol-7-O-β-D-glucopyranoside
7724-09-6, 10367-12-1, 138128-00-4

2-hydroxybenzyl alcohol-7-O-β-D-glucopyranoside

B

D-(-)-salicin
138-52-3

D-(-)-salicin

Conditions
ConditionsYield
With Agrobacterium rhizogenes-induced Pharbitis nil hairy roots; MS medium for 120h;A 50 mg
B 35 mg
salicin pentaacetate
16643-37-1

salicin pentaacetate

D-(-)-salicin
138-52-3

D-(-)-salicin

Conditions
ConditionsYield
With sodium methylate In methanol at 20℃; for 1h; Inert atmosphere;80 mg
β-D-glucose pentaacetate
604-69-3

β-D-glucose pentaacetate

D-(-)-salicin
138-52-3

D-(-)-salicin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: acetic acid; hydrogen bromide; acetic anhydride / 2 h / 20 °C / Inert atmosphere
2: toluene / 3 h / Inert atmosphere; Reflux
3: boron trifluoride diethyl etherate / dichloromethane / 1 h
4: sodium methylate / methanol / 1 h / 20 °C / Inert atmosphere
View Scheme
Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: toluene / 3 h / Inert atmosphere; Reflux
2: boron trifluoride diethyl etherate / dichloromethane / 1 h
3: sodium methylate / methanol / 1 h / 20 °C / Inert atmosphere
View Scheme
3-bromo-2-pyridyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
4336-91-8

3-bromo-2-pyridyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

D-(-)-salicin
138-52-3

D-(-)-salicin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: boron trifluoride diethyl etherate / dichloromethane / 1 h
2: sodium methylate / methanol / 1 h / 20 °C / Inert atmosphere
View Scheme
2-(chloromethyl)phenyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

2-(chloromethyl)phenyl-2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

D-(-)-salicin
138-52-3

D-(-)-salicin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogenchloride / ethanol; chloroform; water / 8 h / 30 °C
2: acetic acid; silver(l) oxide / acetone; water / 48 h / 20 °C
3: sodium methylate / methanol / 2 h / 20 °C
View Scheme
2-(chloromethyl)phenyl-2-O-acetyl-β-D-glucopyranoside

2-(chloromethyl)phenyl-2-O-acetyl-β-D-glucopyranoside

D-(-)-salicin
138-52-3

D-(-)-salicin

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: acetic acid; silver(l) oxide / acetone; water / 48 h / 20 °C
2: sodium methylate / methanol / 2 h / 20 °C
View Scheme
2-methylphenyl-(2,3,4,6-tetra-O-acetyl)-β-D-glucopyranoside
5346-66-7, 32742-28-2, 33535-32-9, 84380-03-0

2-methylphenyl-(2,3,4,6-tetra-O-acetyl)-β-D-glucopyranoside

D-(-)-salicin
138-52-3

D-(-)-salicin

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: bromine; sodium hydrogencarbonate / chloroform / Irradiation
2: hydrogenchloride / ethanol; chloroform; water / 8 h / 30 °C
3: acetic acid; silver(l) oxide / acetone; water / 48 h / 20 °C
4: sodium methylate / methanol / 2 h / 20 °C
View Scheme
Multi-step reaction with 5 steps
1: bromine; sodium hydrogencarbonate / chloroform / Irradiation
2: tetramethlyammonium chloride / acetonitrile / 4 h / Reflux
3: hydrogenchloride / ethanol; chloroform; water / 8 h / 30 °C
4: acetic acid; silver(l) oxide / acetone; water / 48 h / 20 °C
5: sodium methylate / methanol / 2 h / 20 °C
View Scheme
2-(2,3,4,6-tetra-О-acetyl-β-d-glucopyranosyloxy)benzyl bromide
60523-66-2

2-(2,3,4,6-tetra-О-acetyl-β-d-glucopyranosyloxy)benzyl bromide

D-(-)-salicin
138-52-3

D-(-)-salicin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: hydrogenchloride / ethanol; chloroform; water / 8 h / 30 °C
2: acetic acid; silver(l) oxide / acetone; water / 48 h / 20 °C
3: sodium methylate / methanol / 2 h / 20 °C
View Scheme
Multi-step reaction with 4 steps
1: tetramethlyammonium chloride / acetonitrile / 4 h / Reflux
2: hydrogenchloride / ethanol; chloroform; water / 8 h / 30 °C
3: acetic acid; silver(l) oxide / acetone; water / 48 h / 20 °C
4: sodium methylate / methanol / 2 h / 20 °C
View Scheme
acetic anhydride
108-24-7

acetic anhydride

D-(-)-salicin
138-52-3

D-(-)-salicin

salicin pentaacetate
16643-37-1

salicin pentaacetate

Conditions
ConditionsYield
With potassium carbonate In 1,4-dioxane at 60℃; for 16h;95%
benzaldehyde
100-52-7

benzaldehyde

D-(-)-salicin
138-52-3

D-(-)-salicin

4',6'-O-Benzylidene-7-hydroxy-o-tolyl-β-D-glucopyranoside
144364-11-4

4',6'-O-Benzylidene-7-hydroxy-o-tolyl-β-D-glucopyranoside

Conditions
ConditionsYield
With zinc(II) chloride for 8h; Ambient temperature;85%
D-(-)-salicin
138-52-3

D-(-)-salicin

C13H13S5O22(5-)*5Na(1+)

C13H13S5O22(5-)*5Na(1+)

Conditions
ConditionsYield
With pyridine; sulfur trioxide pyridine complex In acetonitrile at 100℃; microwave irradiation;84%
Stage #1: D-(-)-salicin With sulfur trioxide trimethylamine complex; triethylamine In acetonitrile at 90℃; for 0.5h; Microwave irradiation;
Stage #2:
D-(-)-salicin
138-52-3

D-(-)-salicin

A

(2R,3R,5S,6S)-3,5-Dihydroxy-2-hydroxymethyl-6-(2-hydroxymethyl-phenoxy)-tetrahydro-pyran-4-one
808770-08-3

(2R,3R,5S,6S)-3,5-Dihydroxy-2-hydroxymethyl-6-(2-hydroxymethyl-phenoxy)-tetrahydro-pyran-4-one

B

(2R,4R,5R,6S)-2-Hydroxymethyl-6-(2-hydroxymethyl-phenoxy)-dihydro-pyran-3,3,4,5-tetraol
808770-15-2

(2R,4R,5R,6S)-2-Hydroxymethyl-6-(2-hydroxymethyl-phenoxy)-dihydro-pyran-3,3,4,5-tetraol

C

(2R,3R,5S,6S)-2-Hydroxymethyl-6-(2-hydroxymethyl-phenoxy)-tetrahydro-pyran-3,4,4,5-tetraol
808770-11-8

(2R,3R,5S,6S)-2-Hydroxymethyl-6-(2-hydroxymethyl-phenoxy)-tetrahydro-pyran-3,4,4,5-tetraol

Conditions
ConditionsYield
With pyranose dehydrogenase; p-benzoquinone In water-d2 for 24h;A 5%
B 81%
C 8%
Isopropyl fluoroformate
461-71-2

Isopropyl fluoroformate

D-(-)-salicin
138-52-3

D-(-)-salicin

Penta-O-(isopropoxycarbonyl)salicin
124781-64-2

Penta-O-(isopropoxycarbonyl)salicin

Conditions
ConditionsYield
With triethylamine In dichloromethane; dimethyl sulfoxide at 25℃; for 17h;80%
D-(-)-salicin
138-52-3

D-(-)-salicin

Sucrose
57-50-1

Sucrose

A

α-D-glucopyranosyl-(1->4)-salicin
1190089-79-2

α-D-glucopyranosyl-(1->4)-salicin

B

α-D-glucopyranosyl-(1->4)-α-D-glucopyranosyl-(1->4)-salicin
1190089-80-5

α-D-glucopyranosyl-(1->4)-α-D-glucopyranosyl-(1->4)-salicin

Conditions
ConditionsYield
With Deinococcus geothermalis DSM 11300 amylosucrase amylosucrase In tris hydrochloride at 30℃; for 14h; pH=8;A 79%
B 5%
With Neisseria polysaccharea (ATCC 43768) amylosucrase amylosucrase In sodium citrate at 30℃; for 14h; pH=6;
2,2-dimethoxy-propane
77-76-9

2,2-dimethoxy-propane

D-(-)-salicin
138-52-3

D-(-)-salicin

4,6-O-(1-methylethylidene)-D-salicin
346575-75-5

4,6-O-(1-methylethylidene)-D-salicin

Conditions
ConditionsYield
With toluene-4-sulfonic acid In acetonitrile for 2h;72%
benzaldehyde dimethyl acetal
1125-88-8

benzaldehyde dimethyl acetal

D-(-)-salicin
138-52-3

D-(-)-salicin

4',6'-O-Benzylidene-7-hydroxy-o-tolyl-β-D-glucopyranoside
144364-11-4

4',6'-O-Benzylidene-7-hydroxy-o-tolyl-β-D-glucopyranoside

Conditions
ConditionsYield
With toluene-4-sulfonic acid In acetonitrile for 2h;71%
hexadecanoic acid methyl ester
112-39-0

hexadecanoic acid methyl ester

D-(-)-salicin
138-52-3

D-(-)-salicin

6-O-palmitoyl-[2-(hydroxymethyl)phenyl]-β-D-glucopyranoside

6-O-palmitoyl-[2-(hydroxymethyl)phenyl]-β-D-glucopyranoside

Conditions
ConditionsYield
With immobilized lipase B In acetone at 40℃; for 48h;53%
D-(-)-salicin
138-52-3

D-(-)-salicin

5,5'-methylenebis(salicylaldehyde)
3046-82-0

5,5'-methylenebis(salicylaldehyde)

C41H44O16

C41H44O16

Conditions
ConditionsYield
With Amberlyst-15 In dimethyl sulfoxide; benzene for 48h; Inert atmosphere; Dean-Stark;47%
terephthalaldehyde,
623-27-8

terephthalaldehyde,

D-(-)-salicin
138-52-3

D-(-)-salicin

4,6:4',6'-O-terephtalidenebis[2''-(hydroxymethyl)phenyl-β-D-glucopyranoside]

4,6:4',6'-O-terephtalidenebis[2''-(hydroxymethyl)phenyl-β-D-glucopyranoside]

Conditions
ConditionsYield
With Amberlyst-15 In dimethyl sulfoxide; benzene for 48h; Inert atmosphere; Dean-Stark;44%
salicylaldehyde
90-02-8

salicylaldehyde

D-(-)-salicin
138-52-3

D-(-)-salicin

2'-(hydroxymethyl)phenyl 4,6-O-salicylidene-β-D-glucopyranoside

2'-(hydroxymethyl)phenyl 4,6-O-salicylidene-β-D-glucopyranoside

Conditions
ConditionsYield
With Amberlyst-15 In dimethyl sulfoxide; benzene for 48h; Inert atmosphere; Dean-Stark;40%
2,2,2-trichloroethyl butyrate
57392-44-6

2,2,2-trichloroethyl butyrate

D-(-)-salicin
138-52-3

D-(-)-salicin

6'-O-mono-butyrylsalicin

6'-O-mono-butyrylsalicin

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 45℃; for 144h; subtilisin;34%
D-(-)-salicin
138-52-3

D-(-)-salicin

3-Phenylpropionic acid
501-52-0

3-Phenylpropionic acid

6-O-phenylpropionyl-[2-(hydroxymethyl)phenyl]-β-D-glucopyranoside

6-O-phenylpropionyl-[2-(hydroxymethyl)phenyl]-β-D-glucopyranoside

Conditions
ConditionsYield
With immobilized lipase B In tert-butyl alcohol at 60℃; for 34h;32%
4-hydroxyphenylacetate
156-38-7

4-hydroxyphenylacetate

D-(-)-salicin
138-52-3

D-(-)-salicin

6-O-p-OH-phenylacetyl-[(2-hydroxymethyl)phenyl]-β-D-glucopyranoside

6-O-p-OH-phenylacetyl-[(2-hydroxymethyl)phenyl]-β-D-glucopyranoside

Conditions
ConditionsYield
With immobilized lipase B In tert-butyl alcohol at 60℃; for 34h;17%
Conditions
ConditionsYield
With water; palladium Hydrogenation;
trans-1,2-cyclohexandiol
1460-57-7

trans-1,2-cyclohexandiol

D-(-)-salicin
138-52-3

D-(-)-salicin

A

(1R,2R)-trans-1,2-cyclohexanediol-1-O-β-D-glucopyranoside
69501-35-5

(1R,2R)-trans-1,2-cyclohexanediol-1-O-β-D-glucopyranoside

B

(1S,2S)-trans-1,2-cyclohexanediol-1-O-β-D-glucopyranoside
69501-36-6

(1S,2S)-trans-1,2-cyclohexanediol-1-O-β-D-glucopyranoside

Conditions
ConditionsYield
With β-D-glucosidase at 25℃; for 4h; pH=5.0; Yield given. Yields of byproduct given;
2-chloro-1,3,2-dioxaphospholan
822-39-9

2-chloro-1,3,2-dioxaphospholan

D-(-)-salicin
138-52-3

D-(-)-salicin

(2R,3R,4S,5R,6S)-3,4,5-Tris-([1,3,2]dioxaphospholan-2-yloxy)-2-([1,3,2]dioxaphospholan-2-yloxymethyl)-6-[2-([1,3,2]dioxaphospholan-2-yloxymethyl)-phenoxy]-tetrahydro-pyran

(2R,3R,4S,5R,6S)-3,4,5-Tris-([1,3,2]dioxaphospholan-2-yloxy)-2-([1,3,2]dioxaphospholan-2-yloxymethyl)-6-[2-([1,3,2]dioxaphospholan-2-yloxymethyl)-phenoxy]-tetrahydro-pyran

Conditions
ConditionsYield
With pyridine In chloroform-d1 at 25℃;
D-(-)-salicin
138-52-3

D-(-)-salicin

D-Glucose
2280-44-6

D-Glucose

Conditions
ConditionsYield
With β-D-glucosidase of Sclerotium rolfsii In water at 65℃; for 0.5h; enzymic hydrolysis, rate;
D-(-)-salicin
138-52-3

D-(-)-salicin

Salicylic acid phenol glucuronide
7695-70-7

Salicylic acid phenol glucuronide

Conditions
ConditionsYield
With 2,2,6,6-tetramethyl-piperidine-N-oxyl; Carbonate buffer at 20℃; electrochemical reaction: platinum foil anode and a graphite cathode, saturated calomel electrode as reference electrode (Hg/Hg2Cl2/saturated KCl in H2O, +0.20 V vs. SCE), electrolysis at a potential of 0.53 V vs. SCE, charge consumption of 11.2 F/mol; Yield given;

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