D(-)-Salicin supplier | CasNO.138-52-3

Name
2-(Hydroxymethyl)phenyl-beta-D-glucopyranoside
EINECS 205-331-6
CAS No. 138-52-3
Article Data11
CAS DataBase
Density 1.504 g/cm³
Solubility 36 g/L (15°C), 250 g/L (60 °C) in water
Melting Point 197-200 °C
Formula C₁₃H₁₈O₇
Boiling Point 549.1 °C at 760 mmHg
Molecular Weight 286.282
Flash Point 285.9 °C
Transport Information
Appearance white crystals or powder
Safety 36/37-24/25
Risk Codes 43
Molecular Structure
Hazard Symbols Xi
Synonyms Salicyl alcohol glucoside;Salicine;Salicoside;a-D-Glucopyranoside,2-(hydroxymethyl)phenyl;Benzyl alcohol, o-hydroxy-, o-glucoside;2-(Hydroxymethyl)-phenyl-beta-D-glucopyranoside;Saligenin-.beta.-D-glucopyranoside;(2R,3R,4R,5S,6S)-2-(hydroxymethyl)-6-[2-(hydroxymethyl)phenoxy]oxane-3,4,5-triol;2-(hydroxymethyl)-6-[2-(hydroxymethyl)phenoxy]oxane-3,4,5-triol;White willow bark P. E.;α-hydroxy-o-tolyl β-D-glucopyranoside;Salicylaldehyde glycosides;Salicin;White Willow Bark Extract;
PSA 119.61000
LogP -1.64240

Synthetic route

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

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

Conditions

Conditions	Yield
With sodium methylate In methanol at 20℃; for 2h;	99%

: 19764-02-4
2-(hydroxymethyl)phenyl-6-O-acetyl-β-D-glucopyranoside

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

Conditions

Conditions	Yield
With sodium methylate In methanol at 20℃; for 2h;	99%

: 29836-40-6
2-({[(1-hydroxy-6-oxocyclohex-2-en-1-yl)carbonyl]oxy}methyl)phenyl β-D-glucopyranoside 2-benzoate

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

Conditions

Conditions	Yield
With lithium aluminium tetrahydride In tetrahydrofuran at 20℃; for 7h;	46%

: 2280-44-6
D-Glucose

: 90-01-7
salicylic alcohol

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

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

Conditions

Conditions	Yield
With almond β-D-glucosidase In water; acetonitrile at 40℃; for 48h; Enzymatic reaction;	A 9% B 6%

...Expand

: 14581-83-0, 142393-06-4, 148615-67-2
helicin acetate

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

Conditions

Conditions	Yield
With 1,4-dioxane; lithium aluminium tetrahydride; diethyl ether anschl. mit Methanol;

: 29836-41-7
2-[[[(1-hydroxy-6-oxo-2-cyclohexen-1-yl)carbonyl]hydroxy]methyl]phenyl-β-D-glucopyranoside

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

: (+)-6-hydroxycyclohexen-2-one

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

Conditions

Conditions	Yield
enzyme from Populus balsamifera at 27℃; incubation;

...Expand

: pruyanaside A

A: virgaureoside A

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

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

Conditions

Conditions	Yield
With sodium methylate In methanol for 1h; Ambient temperature;

...Expand

: pruyanaside B

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

B: populine

C: henryoside

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

Conditions

Conditions	Yield
With sodium methylate In methanol for 1h; Ambient temperature;

...Expand

: 89-95-2
2-methyl-benzyl alcohol

: 57-50-1
Sucrose

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

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

Conditions

Conditions	Yield
With Agrobacterium rhizogenes-induced Pharbitis nil hairy roots; MS medium for 120h;	A 50 mg B 35 mg

...Expand

: 16643-37-1
salicin pentaacetate

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

Conditions

Conditions	Yield
With sodium methylate In methanol at 20℃; for 1h; Inert atmosphere;	80 mg

: 604-69-3
β-D-glucose pentaacetate

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

Conditions

Conditions	Yield
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

: 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

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

Conditions

Conditions	Yield
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

: 4336-91-8
3-bromo-2-pyridyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside

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

Conditions

Conditions	Yield
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

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

Conditions

Conditions	Yield
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

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

Conditions

Conditions	Yield
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

: 5346-66-7, 32742-28-2, 33535-32-9, 84380-03-0
2-methylphenyl-(2,3,4,6-tetra-O-acetyl)-β-D-glucopyranoside

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

Conditions

Conditions	Yield
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

: 60523-66-2
2-(2,3,4,6-tetra-О-acetyl-β-d-glucopyranosyloxy)benzyl bromide

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

Conditions

Conditions	Yield
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

: 108-24-7
acetic anhydride

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

: 16643-37-1
salicin pentaacetate

Conditions

Conditions	Yield
With potassium carbonate In 1,4-dioxane at 60℃; for 16h;	95%

: 100-52-7
benzaldehyde

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

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

Conditions

Conditions	Yield
With zinc(II) chloride for 8h; Ambient temperature;	85%

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

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

Conditions

Conditions	Yield
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:

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

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

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

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

Conditions

Conditions	Yield
With pyranose dehydrogenase; p-benzoquinone In water-d2 for 24h;	A 5% B 81% C 8%

...Expand

: 461-71-2
Isopropyl fluoroformate

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

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

Conditions

Conditions	Yield
With triethylamine In dichloromethane; dimethyl sulfoxide at 25℃; for 17h;	80%

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

: 57-50-1
Sucrose

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

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

Conditions

Conditions	Yield
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;

...Expand

: 77-76-9
2,2-dimethoxy-propane

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

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

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In acetonitrile for 2h;	72%

: 1125-88-8
benzaldehyde dimethyl acetal

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

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

Conditions

Conditions	Yield
With toluene-4-sulfonic acid In acetonitrile for 2h;	71%

: 112-39-0
hexadecanoic acid methyl ester

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

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

Conditions

Conditions	Yield
With immobilized lipase B In acetone at 40℃; for 48h;	53%

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

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

: C41H44O16

Conditions

Conditions	Yield
With Amberlyst-15 In dimethyl sulfoxide; benzene for 48h; Inert atmosphere; Dean-Stark;	47%

: 623-27-8
terephthalaldehyde,

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

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

Conditions

Conditions	Yield
With Amberlyst-15 In dimethyl sulfoxide; benzene for 48h; Inert atmosphere; Dean-Stark;	44%

: 90-02-8
salicylaldehyde

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

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

Conditions

Conditions	Yield
With Amberlyst-15 In dimethyl sulfoxide; benzene for 48h; Inert atmosphere; Dean-Stark;	40%

: 57392-44-6
2,2,2-trichloroethyl butyrate

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

: 6'-O-mono-butyrylsalicin

Conditions

Conditions	Yield
In N,N-dimethyl-formamide at 45℃; for 144h; subtilisin;	34%

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

: 501-52-0
3-Phenylpropionic acid

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

Conditions

Conditions	Yield
With immobilized lipase B In tert-butyl alcohol at 60℃; for 34h;	32%

: 156-38-7
4-hydroxyphenylacetate

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

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

Conditions

Conditions	Yield
With immobilized lipase B In tert-butyl alcohol at 60℃; for 34h;	17%

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

: 7234-31-3, 10236-48-3, 19887-82-2, 31909-75-8, 33526-62-4
o-tolyl-β-D-glucopyranoside

Conditions

Conditions	Yield
With water; palladium Hydrogenation;

: 1460-57-7
trans-1,2-cyclohexandiol

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

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

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

Conditions

Conditions	Yield
With β-D-glucosidase at 25℃; for 4h; pH=5.0; Yield given. Yields of byproduct given;

...Expand

: 822-39-9
2-chloro-1,3,2-dioxaphospholan

: 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

Conditions

Conditions	Yield
With pyridine In chloroform-d1 at 25℃;

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

: 2280-44-6
D-Glucose

Conditions

Conditions	Yield
With β-D-glucosidase of Sclerotium rolfsii In water at 65℃; for 0.5h; enzymic hydrolysis, rate;

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

: 7695-70-7
Salicylic acid phenol glucuronide

Conditions

Conditions	Yield
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;

D(-)-Salicin Chemical Properties

IUPAC Name: (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-[2-(hydroxymethyl)phenoxy]oxane-3,4,5-triol
Synonyms of D(-)-Salicin (CAS NO.138-52-3): 2-(Hydroxymethyl)phenyl beta-D-glucopyranoside ; Benzyl alcohol, o-hydroxy-, o-glucoside ; Salicine ; Salicoside ; Salicyl alcohol glucoside ; o-(Hydroxymethyl)phenyl beta-D-glucopyranoside ; B-D-Glucopyranoside, 2-(hydroxymethyl)phenyl ; Salicin (6CI,8CI)
CAS NO: 138-52-3
Molecular Formula: C₁₃H₁₈O₇
Molecular Weight: 286.28
Molecular Structure:
EINECS: 205-331-6
H bond acceptors: 7
H bond donors: 5
Freely Rotating Bonds: 9
Polar Surface Area: 64.61 Å²
Index of Refraction: 1.638
Molar Refractivity: 68.41 cm³
Molar Volume: 190.3 cm³
Surface Tension: 70.1 dyne/cm
Density: 1.504 g/cm³
Flash Point: 285.9 °C
Enthalpy of Vaporization: 87.22 kJ/mol
Boiling Point: 549.1 °C at 760 mmHg
Vapour Pressure: 6.85E-13 mmHg at 25°C
Melting point 197-200°C
Alpha: -61.5 º (c=5, water)
Water solubility: 36 g/L (15°C), 250 g/L (60 °C)
Storage temp: Store at RT.
Appearance: white crystals or powder
Stability: Stability Stable, but light sensitive. Incompatible with strong oxidizing agents.
Product Categories of D(-)-Salicin (CAS NO.138-52-3): Sugars, Carbohydrates & Glucosides;Biochemistry;Glucose;Glycosides;Sugars;Natural Plant Extract;Herbs & Natural Remedies

D(-)-Salicin Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD	intraperitoneal	> 500mg/kg (500mg/kg)		"Summary Tables of Biological Tests," National Research Council Chemical-Biological Coordination Center. Vol. 6, Pg. 63, 1954.

D(-)-Salicin Safety Profile

Safety Information of D(-)-Salicin (CAS NO.138-52-3):
The Hazard Codes: Xi
The Risk Statements: 43
43: May cause sensitization by skin contact
The Safety Statements: 36/37-24/25
24/25: Avoid contact with skin and eyes
36/37: Wear suitable protective clothing and gloves
WGK Germany: 3
RTECS: LZ5901700
F: 3-10
HS Code: 29389090

D(-)-Salicin Specification

General Information: As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media: Use water spray, dry chemical, carbon dioxide, or chemical foam.
Handling: Avoid breathing dust, vapor, mist, or gas. Avoid contact with skin and eyes. Avoid ingestion and inhalation.
Storage: Store in a cool, dry place. Store in a tightly closed container.

Product Name

2-(Hydroxymethyl)phenyl-beta-D-glucopyranoside

Synthetic route

D(-)-Salicin Chemical Properties

D(-)-Salicin Toxicity Data With Reference

D(-)-Salicin Safety Profile

D(-)-Salicin Specification

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