29836-26-8

Basic information

• Product Name: Octyl-beta-D-glucopyranoside
• Synonyms: N-OCTYL GLUCOSIDE;N-OCTYL-B-D-GLUCOSIDE;N-OCTYL-BETA-D-GLC;N-OCTYL-BETA-D-GLUCOPYRANOSIDE;N-OCTYL-BETA-D-GLUCOSIDE;.beta.-D-Glucopyranoside, octyl;n-octyl-á-d-glucopyranoside;n-octyl-á-d-glucoside
• CAS NO: 29836-26-8
• Molecular Formula: C₁₄H₂₈O₆
• Molecular Weight: 292.37
• EINECS: 249-887-8
• Product Categories: Biochemistry;Glucose;Glycosides;Sugars;Nonionic Surfactants (for Biochemistry);Surfactants (for Biochemistry);Carbohydrates & Derivatives;Detergents;detergent
• Mol File: 29836-26-8.mol
• Article Data: 47

Chemical Properties

• Melting Point: 105 °C
• Boiling Point: 354.3°C (rough estimate)
• Flash Point: 228.4 °C
• Appearance: White/Crystalline Powder and Chunks
• Density: 1.0869 (rough estimate)
• Vapor Pressure: 3.72E-10mmHg at 25°C
• Refractive Index: -27 ° (C=1, MeOH)
• Storage Temp.: 2-8°C
• Solubility: DMSO (Slightly), Water (Slightly)
• PKA: 12.95±0.70(Predicted)
• Water Solubility: 3 g/10 mL
• Sensitive: Hygroscopic
• Stability: Hygroscopic
• Merck: 14,6767
• BRN: 84118
• CAS DataBase Reference: Octyl-beta-D-glucopyranoside(CAS DataBase Reference)
• NIST Chemistry Reference: Octyl-beta-D-glucopyranoside(29836-26-8)
• EPA Substance Registry System: Octyl-beta-D-glucopyranoside(29836-26-8)

Safety Data

• Statements: 36/37/38
• Safety Statements: 24/25
• WGK Germany: 3
• Hazardous Substances Data: 29836-26-8(Hazardous Substances Data)

Usage

Chemical Properties

white crystalline powder and chunks

Uses

Different sources of media describe the Uses of 29836-26-8 differently. You can refer to the following data:
1. A nonionic detergent for the solubilization of membrane bound protein.
2. Unlike many other detergents, octyl glucoside is a pure, single compound of defined structure. Very effective for insulin binding and solubilization studies of membran
3. Detergent and surfactant for biological systems.

Purification Methods

Purify octyl--D-glucopyranoside by recrystallisation from Me2CO. It is hygroscopic and should be stored in a well-stoppered container. [Noller & Rockwell J Am Chem Soc 6 0 2076 1938, Pigman & Richtmyer J Am Chem Soc 64 369 1942.] It is a UV transparent non-ionic dialysable detergent for solubilising membrane proteins. The D-isomer with [] D 20 +118o (c 1, MeOH) has similar solubilising properties. [Lazo & Quinn Anal Biochem 102 68 1980, Stubbs et al. Biochim Biophys Acta 426 46 1976, Beilstein 17/7 V 38.]

InChI:InChI=1/C14H28O6/c1-2-3-4-5-6-7-8-19-14-13(18)12(17)11(16)10(9-15)20-14/h10-18H,2-9H2,1H3

Synthetic route

octyl (2,3,4,6-tetra-O-acetyl)-β-D-glucopyranoside (38954-67-5) → n-octyl β-D-glucopyranoside (29836-26-8)

Conditions	Yield
With sodium methylate In methanol at 20℃; for 3h; Zemplen reaction;	100%
With sodium methylate In methanol for 2h; Ambient temperature;	99%
With sodium methylate In methanol at 20℃; Inert atmosphere;	91%

β-D-glucose (492-61-5) + octanol (111-87-5) → n-octyl β-D-glucopyranoside (29836-26-8)

Conditions	Yield
With citrate buffer; Aerosol-OT; β-glucosidase In octane at 20℃; for 120h; pH=5.5;	40%
With almond meal In water at 50℃; for 168h; Thermodynamic data; Equilibrium constant; Enzymatic reaction;	4.05%
With almond meal cross-linked with glutaraldehyde In water at 50℃; for 168h; Equilibrium constant; Enzymatic reaction;

D-Glucose (2280-44-6) + octanol (111-87-5) → octyl alpha-D-glucopyranoside (29781-80-4) + n-octyl β-D-glucopyranoside (29836-26-8)

Conditions	Yield
With sulfuric acid In 1,4-dioxane Yields of byproduct given;	A 30% B n/a
With boron trifluoride diethyl etherate In tetrahydrofuran for 55h; Ambient temperature; Yield given. Yields of byproduct given;
With acetyl chloride at 120℃; for 0.333333h; microwave irradiation;

D-Glucose (2280-44-6) + octanol (111-87-5) → n-octyl β-D-glucopyranoside (29836-26-8)

Conditions	Yield
With immobilized β-glucosidase G 0395 from almonds (EC 3.2.1.21) In water at 20℃; for 144h;	18%
With almond β-glucosidase immobilised with ENTP-4000 In water at 50℃; for 96h;	8.2%
In water; acetonitrile at 40℃; for 72h; 90percent CH3CN, almond β-D-glucosidase; Yield given;
With almond β-D-glycosidase immobilized on Amberlite XAD-4; sodium chloride In acetonitrile at 50℃; Kinetics; Further Variations:; Solvents; Reaction partners; Enzymatic reaction;
With almond β-glucosidase immobilized on Amberlite XAD-4; barium(II) chloride In N,N-dimethyl-formamide at 50℃; Enzymatic reaction;

octanol (111-87-5) + D-glucose (50-99-7) → n-octyl β-D-glucopyranoside (29836-26-8)

Conditions	Yield
With Amberlite IR-120 (H+) resin for 0.133333h; Microwave irradiation;	15%
With β-glucosidase immobilized on polyamine microspheres In aq. phosphate buffer; tert-butyl alcohol at 50℃; for 48h; pH=6; Catalytic behavior; Kinetics; Concentration; Reagent/catalyst; Solvent; Enzymatic reaction;
With recombinant β-glucosidase from Microcerotermes annandalei In aq. phosphate buffer at 30℃; for 144h;

Cellobiose (133-99-3, 490-37-9, 2152-98-9, 4482-75-1, 5965-66-2, 13299-27-9, 13360-52-6, 14641-93-1, 15548-43-3, 16462-44-5, 16984-36-4, 16984-38-6, 20869-27-6, 22688-72-8, 27452-49-9, 29276-55-9, 30608-12-9, 34481-13-5, 37169-60-1, 37169-64-5, 64234-01-1, 64234-02-2, 75281-88-8, 80446-85-1, 84413-57-0, 92344-56-4, 93221-87-5, 93301-77-0, 94799-29-8, 100427-98-3, 100428-00-0, 101312-82-7, 102046-24-2, 102046-25-3, 109432-00-0, 109432-02-2, 109432-04-4, 109432-08-8, 135268-49-4, 138231-26-2, 140461-59-2, 145414-22-8, 145414-26-2, 146339-75-5, 146339-76-6, 149116-55-2, 528-50-7) + octanol (111-87-5) → D-Glucose (2280-44-6) + n-octyl β-D-glucopyranoside (29836-26-8)

Conditions	Yield
With almond β-glucosidase In acetate buffer; acetonitrile at 50℃; for 72h; pH=4.4;	A n/a B 14.4%

octanol (111-87-5) + phenyl-β-D-glucopyranoside (1464-44-4) → n-octyl β-D-glucopyranoside (29836-26-8)

Conditions	Yield
With phosphate buffer; lactase from Kluyveromyces lactis In nitrobenzene at 50℃; for 1h;	13%

octanol (111-87-5) + butyl-α-D-glucopyranoside (5391-18-4, 25320-93-8, 39824-09-4, 95531-15-0, 143289-25-2, 146453-36-3, 148347-27-7) → D-glucose (50-99-7) + octyl alpha-D-glucopyranoside (29781-80-4) + levoglucosan (498-07-7) + butyl-D-glucofuranoside + n-octyl β-D-glucopyranoside (29836-26-8)

Conditions	Yield
With Amberlyst 15DRY at 110℃; for 24h; Sealed vial; Ionic liquid;	A 15 %Chromat. B 38 %Chromat. C 10% D 6% E 21 %Chromat.

octanol (111-87-5) + 4-nitrophenyl-β-D-glucoside (2492-87-7) → n-octyl β-D-glucopyranoside (29836-26-8)

Conditions	Yield
With phosphate buffer; β-glucosidase at 30℃; for 17h; pH=5;	2%
With water; almond β-glucosidase In acetate buffer; N,N-dimethyl-formamide at 50℃; pH=5.0; Kinetics; Further Variations:; Solvents; enzyme immobilized on Celite R640<*>;

Cellobiose (133-99-3, 490-37-9, 2152-98-9, 4482-75-1, 5965-66-2, 13299-27-9, 13360-52-6, 14641-93-1, 15548-43-3, 16462-44-5, 16984-36-4, 16984-38-6, 20869-27-6, 22688-72-8, 27452-49-9, 29276-55-9, 30608-12-9, 34481-13-5, 37169-60-1, 37169-64-5, 64234-01-1, 64234-02-2, 75281-88-8, 80446-85-1, 84413-57-0, 92344-56-4, 93221-87-5, 93301-77-0, 94799-29-8, 100427-98-3, 100428-00-0, 101312-82-7, 102046-24-2, 102046-25-3, 109432-00-0, 109432-02-2, 109432-04-4, 109432-08-8, 135268-49-4, 138231-26-2, 140461-59-2, 145414-22-8, 145414-26-2, 146339-75-5, 146339-76-6, 149116-55-2, 528-50-7) + octanol (111-87-5) → n-octyl β-D-glucopyranoside (29836-26-8)

Conditions	Yield
In water at 30℃; for 48h; β-glucosidase from Trichoderma viride; Yield given;

D-Glucose (2280-44-6) + octanol (111-87-5) → octyl alpha-D-glucopyranoside (29781-80-4) + Octyl-β-D-glucofuranoside + n-octyl α-D-glucofuranoside + n-octyl β-D-glucopyranoside (29836-26-8)

Conditions	Yield
With iron(III) chloride In tetrahydrofuran for 24h; Product distribution; Ambient temperature; various solvents and promoters investigated;
With H+ ion exchanged zeolite Y at 130℃; Reagent/catalyst;

n-octyl α-D-glucopyranosyl-(1->4)-β-D-glucopyranoside (82494-08-4) → (2S,3S,4R,5R,6R)-4,5-Dihydroxy-6-octyloxy-3-((2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-carboxylic acid + (2S,3S,4S,5R,6S)-6-((2R,3S,4R,5R,6R)-4,5-Dihydroxy-2-hydroxymethyl-6-octyloxy-tetrahydro-pyran-3-yloxy)-3,4,5-trihydroxy-tetrahydro-pyran-2-carboxylic acid + (2R,3R)-3-[(R)-Carboxy-((2R,3S,4R,5R,6R)-4,5-dihydroxy-2-hydroxymethyl-6-octyloxy-tetrahydro-pyran-3-yloxy)-methoxy]-2,4-dihydroxy-butyric acid + C20H34O13 + (2R,3R)-3-((R)-Carboxy-octyloxy-methoxy)-2,4-dihydroxy-butyric acid + n-octyl β-D-glucopyranoside (29836-26-8)

Conditions	Yield
With sodium bromate; phosphate buffer; Ru(azpy)2(H2O)22+ at 60℃; Product distribution; Mechanism; other pH: 3, 4.5, 8.5, 10;

octyl-O-acetyl-β-D-glucopyranoside> → n-octyl β-D-glucopyranoside (29836-26-8)

Conditions	Yield
With methanol; sodium methylate
With methanol; barium methoxide

octyl 3,4,6-tri-O-benzyl-β-D-glucopyranoside (185549-56-8) → n-octyl β-D-glucopyranoside (29836-26-8)

Conditions	Yield
With hydrogen; palladium on activated charcoal at 20℃;

N,N'-Bis-(6-amino-pyridin-2-yl)-isophthalamide; compound with (2R,3S,4S,5R,6R)-2-hydroxymethyl-6-octyloxy-tetrahydro-pyran-3,4,5-triol → 1,3-bis-[[(6-amino-pyridin-2-yl)amino]carbonyl]benzene (112817-57-9) + n-octyl β-D-glucopyranoside (29836-26-8)

Conditions	Yield
In chloroform-d1 at 24.85℃; Equilibrium constant;

N,N'-Bis-(6-amino-pyridin-2-yl)-isophthalamide; compound with (2R,3S,4S,5R,6R)-2-hydroxymethyl-6-octyloxy-tetrahydro-pyran-3,4,5-triol → 1,3-bis-[[(6-amino-pyridin-2-yl)amino]carbonyl]benzene (112817-57-9) + n-octyl β-D-glucopyranoside (29836-26-8)

Conditions	Yield
In chloroform-d1 at 24.85℃; Equilibrium constant;

N-(6-Amino-pyridin-2-yl)-2-{3-[(6-amino-pyridin-2-ylcarbamoyl)-methoxy]-phenoxy}-acetamide; compound with (2R,3S,4S,5R,6R)-2-hydroxymethyl-6-octyloxy-tetrahydro-pyran-3,4,5-triol → n-octyl β-D-glucopyranoside (29836-26-8) + 1,3-bis-[[(6-amino-pyridin-2-yl)amino]carbonyl-methyloxy]benzene

Conditions	Yield
In chloroform-d1 at 24.85℃; Equilibrium constant;

Benzene-1,3,5-tricarboxylic acid tris-[(6-ethyl-pyridin-2-yl)-amide]; compound with (2R,3S,4S,5R,6R)-2-hydroxymethyl-6-octyloxy-tetrahydro-pyran-3,4,5-triol → n-octyl β-D-glucopyranoside (29836-26-8) + N,N',N''-tris(6-ethylpyridin-2-yl)benzene-1,3,5-tricarbonamide (797818-00-9)

Conditions	Yield
In chloroform-d1 at 24.85℃; Equilibrium constant;

C33H42N6*2C14H28O6 → n-octyl β-D-glucopyranoside (29836-26-8) + 1,3,5-tris[(4,6-dimethylpyridin-2-yl)aminomethyl]-2,4,6-trimethylbenzene (485831-83-2)

Conditions	Yield
In chloroform-d1 at 24.85℃; Equilibrium constant;

C33H42N6*C14H28O6 → n-octyl β-D-glucopyranoside (29836-26-8) + 1,3,5-tris[(4,6-dimethylpyridin-2-yl)aminomethyl]-2,4,6-trimethylbenzene (485831-83-2)

Conditions	Yield
In chloroform-d1 at 24.85℃; Equilibrium constant;

{[3,5-Bis-(4,6-dimethyl-pyridin-2-ylcarbamoyl)-benzoyl]-ethoxycarbonylmethyl-amino}-acetic acid ethyl ester; compound with (2R,3S,4S,5R,6R)-2-hydroxymethyl-6-octyloxy-tetrahydro-pyran-3,4,5-triol → n-octyl β-D-glucopyranoside (29836-26-8) + N-di(ethoxycarbonylmethyl)-N',N''-bis(4,6-dimethylpyridin-2-yl)benzene-1,3,5-tricarbonamide

Conditions	Yield
In chloroform-d1 at 24.85℃; Equilibrium constant;

2C30H39N9*C14H28O6 → n-octyl β-D-glucopyranoside (29836-26-8) + 1,3,5-tris[(6-aminopyridin-2-yl)aminomethyl]-2,4,6-triethylbenzene (797818-02-1)

Conditions	Yield
In chloroform-d1 at 24.85℃; Equilibrium constant;

C30H39N9*C14H28O6 → n-octyl β-D-glucopyranoside (29836-26-8) + 1,3,5-tris[(6-aminopyridin-2-yl)aminomethyl]-2,4,6-triethylbenzene (797818-02-1)

Conditions	Yield
In chloroform-d1 at 24.85℃; Equilibrium constant;

C36H48N6*C14H28O6 → n-octyl β-D-glucopyranoside (29836-26-8) + 1,3,5-tris-[(4,6-dimethyl-pyridin-2-yl)-aminomethyl]-2,4,6-triethylbenzene (797818-01-0)

Conditions	Yield
In chloroform-d1 at 24.85℃; Equilibrium constant;

C36H48N6*2C14H28O6 → n-octyl β-D-glucopyranoside (29836-26-8) + 1,3,5-tris-[(4,6-dimethyl-pyridin-2-yl)-aminomethyl]-2,4,6-triethylbenzene (797818-01-0)

Conditions	Yield
In chloroform-d1 at 24.85℃; Equilibrium constant;

2-{3,5-Bis-[(4,6-dimethyl-pyridin-2-ylcarbamoyl)-methyl]-2,4,6-trimethyl-phenyl}-N-(4,6-dimethyl-pyridin-2-yl)-acetamide; compound with (2R,3S,4S,5R,6R)-2-hydroxymethyl-6-octyloxy-tetrahydro-pyran-3,4,5-triol → n-octyl β-D-glucopyranoside (29836-26-8) + 2-[3,5-bis[(4,6-dimethylpyridin-2-ylcarbamoyl)methyl]-2,4,6-trimethylphenyl]-N-(4,6-dimethylpyridin-2-yl)acetamide (797818-03-2)

Conditions	Yield
In chloroform-d1 at 24.85℃; Equilibrium constant;

benzoyl chloride (98-88-4) + n-octyl β-D-glucopyranoside (29836-26-8) → octyl 4-O-benzoyl-β-D-glucopyranoside (1394172-54-3)

Conditions	Yield
With (2S,5S)-2,5-bis[[(2S)-3-(1H-indol-3-yl)-1-(octyloxy)-1-oxopropan-2-ylamino]carbonyl]-1-(pyridin-4-yl)pyrrolidine; N-ethyl-N,N-diisopropylamine; Trimethylacetic acid In chloroform at -20℃; for 0.25h; Catalytic behavior; Reagent/catalyst;	87%

benzoyl chloride (98-88-4) + n-octyl β-D-glucopyranoside (29836-26-8) → n-octyl 2,3,4,6-tetra-O-benzoyl-β-D-glucopyranoside

Conditions	Yield
With pyridine; dmap at 0 - 20℃; for 12h;	87%

2,2-dimethoxy-propane (77-76-9) + n-octyl β-D-glucopyranoside (29836-26-8) → n-octyl 4,6-O-isopropylidene-β-D-glucopyranoside

Conditions	Yield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide at 20℃; for 5h;	83%

N-Cbz-L-Phe (1161-13-3) + n-octyl β-D-glucopyranoside (29836-26-8) → octyl 4-O-((S)-2-benzyloxycarbonylamino-3-phenylpropanoyl)-β-D-glucopyranoside (1194234-22-4)

Conditions

Yield

Stage #1: N-Cbz-L-Phe With pivaloyl chloride; N-ethyl-N,N-diisopropylamine In chloroform at 20℃; for 1h; Inert atmosphere; Stage #2: n-octyl β-D-glucopyranoside With 2,4,6-trimethyl-pyridine; (2S,5S)-2,5-bis[[(2S)-3-(1H-indol-3-yl)-1-(octyloxy)-1-oxopropan-2-ylamino]carbonyl]-1-(pyridin-4-yl)pyrrolidine In chloroform at -20℃; for 24h; Catalytic behavior; Reagent/catalyst; Inert atmosphere; regioselective reaction;

82%

2-Methylpropionic anhydride (97-72-3) + n-octyl β-D-glucopyranoside (29836-26-8) → C18H34O8 + C18H34O8 + C18H34O8 + C18H34O8

Conditions	Yield
Stage #1: n-octyl β-D-glucopyranoside With 2,4,6-trimethyl-pyridine; (2S,5S)-2,5-bis[[(2S)-3-(1H-indol-3-yl)-1-(octyloxy)-1-oxopropan-2-ylamino]carbonyl]-1-(pyridin-4-yl)pyrrolidine In chloroform; dimethyl sulfoxide at -20℃; Stage #2: 2-Methylpropionic anhydride In chloroform; dimethyl sulfoxide at -20℃; for 24h; Overall yield = 63 %; regioselective reaction;	A 78% B n/a C n/a D n/a

2-Methylpropionic anhydride (97-72-3) + n-octyl β-D-glucopyranoside (29836-26-8) → C18H34O8 + C18H34O8 + C18H34O8

Conditions	Yield
Stage #1: n-octyl β-D-glucopyranoside With 2,4,6-trimethyl-pyridine; (2S,5S)-2,5-bis[[(2S)-3-(1H-indol-3-yl)-1-(octyloxy)-1-oxopropan-2-ylamino]carbonyl]-1-(pyridin-4-yl)pyrrolidine In chloroform; dimethyl sulfoxide at -20℃; Stage #2: 2-Methylpropionic anhydride In chloroform; dimethyl sulfoxide at -20℃; for 24h; Overall yield = 67 %; regioselective reaction;	A 78% B n/a C n/a

n-octyl β-D-glucopyranoside (29836-26-8) → C14H26O6

Conditions	Yield
With 2,5-Diisopropylphenol; oxygen In acetonitrile at 60℃; under 760.051 Torr; chemoselective reaction;	74%

1,2-anhydro-3,4,6-tri-O-benzyl-D-galactopyranose (112289-38-0) + n-octyl β-D-glucopyranoside (29836-26-8) → C41H56O11

Conditions	Yield
With 4-nitrophenylboronic acid In acetonitrile at -20℃; for 24h; Inert atmosphere; regioselective reaction;	71%

1,2-anhydro-3,4,6-tri-O-benzyl-β-D-mannopyranose (74372-90-0, 112289-38-0, 135202-48-1, 148888-66-8, 71696-32-7) + n-octyl β-D-glucopyranoside (29836-26-8) → C41H56O11 + C41H56O11

Conditions	Yield
With 4-nitrophenylboronic acid; water In acetonitrile at 20℃; for 22h; Inert atmosphere; regioselective reaction;	A 1% B 70%

acetic anhydride (108-24-7) + p-toluenesulfonyl chloride (98-59-9) + n-octyl β-D-glucopyranoside (29836-26-8) → octyl 2,3,4-tri-O-acetyl-6-O-tosyl-β-D-glucopyranoside (1435740-69-4)

Conditions	Yield
Stage #1: p-toluenesulfonyl chloride; n-octyl β-D-glucopyranoside With pyridine at -5℃; Stage #2: acetic anhydride at 0 - 23℃; for 5h;	68%
Stage #1: p-toluenesulfonyl chloride; n-octyl β-D-glucopyranoside With pyridine at -5℃; Stage #2: acetic anhydride at 0 - 20℃; for 5h;	68%

C6H10IO3P + n-octyl β-D-glucopyranoside (29836-26-8) → diallyl octyl β-D-glucopyranoside phosphate

Conditions	Yield
With dmap In dichloromethane at 20℃; for 4h; Inert atmosphere;	67%

N-(benzyloxycarbonyl)-L-phenylalanine benzyl ester (60379-01-3) + n-octyl β-D-glucopyranoside (29836-26-8) → (S)-2-Benzyloxycarbonylamino-3-phenyl-propionic acid (2R,3S,4S,5R,6R)-3,4,5-trihydroxy-6-octyloxy-tetrahydro-pyran-2-ylmethyl ester

Conditions	Yield
With subtilisin-CLEC In acetonitrile at 40℃; for 144h;	65%

Upstream product

• 111-87-5 octanol 
• 1464-44-4 phenyl-β-D-glucopyranoside 
• 2280-44-6 D-Glucose 
• 71091-89-9 n-octyl triflate 
• 128299-96-7 n-octyl 2,3,4,6-tetra-O-acetyl-β-D-mannopyranoside 
• 530-26-7 D-Mannose 
• 267890-72-2 n-octyl 2,3,4,6-tetra-O-benzyl-β-D-mannopyranoside 
• 5996-00-9 β-gentiobiose 
• 3947-62-4 2,3,4,6-tetra-O-acetyl-β-D-glucopyranose 
• 50-99-7 D-glucose 
• 69984-73-2 (2R,3S,4S,5R,6R)-2-Hydroxymethyl-6-nonyloxy-tetrahydro-pyran-3,4,5-triol 
• 78617-12-6 n-heptyl beta-D-glucopyranoside 
• 39824-11-8 n-hexyl-β-D-glucopyranoside 
• 25320-96-1 O-n-pentyl β-D-glucopyranoside 

Downstream Products

• 724771-79-3 octyl 2,3,4-tri-O-acetyl-6-O-trityl-β-D-glucopyranoside 
• 25320-91-6 propyl β-D-glucopyranoside 
• 5391-18-4 n-butyl β-D-glucopyranoside 
• 25320-96-1 O-n-pentyl β-D-glucopyranoside 
• 39824-11-8 n-hexyl-β-D-glucopyranoside 
• 78617-12-6 n-heptyl beta-D-glucopyranoside 
• 69984-73-2 (2R,3S,4S,5R,6R)-2-Hydroxymethyl-6-nonyloxy-tetrahydro-pyran-3,4,5-triol 
• 1164120-19-7 C₁₄H₂₈O₆*C₄₇H₅₆N₈ 
• 1173893-91-8 C₃₃H₄₂O₆ 
• 1020663-99-3 C₁₄H₂₈O₆*C₂₄H₁₈N₆ 

Relevant articles and documents

Enzymatic synthesis of octyl glucoside catalyzed by almond β-glucosidase in organic media

The synthesis of n-octyl-β-D-glucopyranoside can be performed by direct condensation of 1-octanol and glucose, catalyzed by immobilized almond β-glucosidase, using solid glucose suspended in 1-octanol as a reaction media. Both the rate of reaction and the conversion could be enhanced by using acetonitrile and N,N-dimethylformamide (DMF) as co-solvents, the latter giving the best results. The rate of reaction was dependent on the concentration of DMF and on the initial water activity (aw), with higher water activity fostering faster reactions. The rate increased with DMF concentration, up to 20% DMF, but diminished rapidly at higher concentrations. Product concentration could be increased from 40 to 100 mM by going from 0 to 20% DMF; however, it was not sensitive to the initial water activity.

Synthesis of octyl glucopyranoside by almond β-glucosidase adsorbed onto Celite R-640

The synthesis of octyl glucoside from p-nitrophenyl glucopyranoside (p-NPG) and 1-octanol was carried out with almond β-glucosidase adsorbed onto Celite R-640. The influence of the amount of water added to the system as well as the addition of co-solvents

Development of novel inhibitors specific for human heparanase-1

The octylglycosides 1-3 having heparan sulfate fragments were designed as inhibitors specific for human heparanase-1. Inhibition experiments for the heparanase revealed the inhibitory effects of 1 and 3 (IC50 = 6 and 1.4mM, respectively). It was difficult for compound 2 to inhibit the heparanase activity. Furthermore, the inhibitory action of 3 was specific for the heparanase, whereas 1 and 2 also inhibited the hydrolysis activity of exoenzyme β-glucuronidase from bovine liver.

Estrogenicity of octyl glucoside synthesized by direct glucosidation as non-endocrine disruptive surfactant

The estrogenicity of octyl glucoside was studied with its preparation method using microporous zeolites. Its estrogenicity was estimated using E-assay method to confirm the possibility as nonendocrine disruptive surfactant. The octyl glucoside was synthesized from D-glucose with 1-octanol by direct glucosidation. The high conversion of D-glucose was obtained on H-FAU zeolite which has a mild acid strength. The conversion and yield were improved with increasing of acid site amount of the zeolite catalysts. The octyl glucopyranoside is more hydrophilic than nonylphenol and has a high wettability. The octyl glucosides represented extremely lower estrogenic cell proliferation compared with nonylphenol.

Molecular Characterization and Potential Synthetic Applications of GH1 β-Glucosidase from Higher Termite Microcerotermes annandalei

A novel β-glucosidase from higher termite Microcerotermes annandalei (MaBG) was obtained via a screening method targeting β-glucosidases with increased activities in the presence of glucose. The purified natural MaBG showed a subunit molecular weight of 55?kDa and existed in a native form as a dimer without any glycosylation. Gene-specific primers designed from its partial amino acid sequences were used to amplify the corresponding 1,419-bp coding sequence of MaBG which encodes a 472-amino acid glycoside hydrolase family 1 (GH1) β-glucosidase. When expressed in Komagataella pastoris, the recombinant MaBG appeared as a ~ 55-kDa protein without glycosylation modifications. Kinetic parameters as well as the lack of secretion signal suggested that MaBG is an intracellular enzyme and not involved in cellulolysis. The hydrolytic activities of MaBG were enhanced in the presence of up to 3.5-4.5 M glucose, partly due to its strong transglucosylation activity, which suggests its applicability in biosynthetic processes. The potential synthetic activities of the recombinant MaBG were demonstrated in the synthesis of para-nitrophenyl-β-D-gentiobioside via transglucosylation and octyl glucoside via reverse hydrolysis. The information obtained from this study has broadened our insight into the functional characteristics of this variant of?termite GH1 β-glucosidase and its applications in bioconversion and biotechnology.