78617-12-6

Basic information

• Product Name: HEPTYL-BETA-D-GLUCOPYRANOSIDE
• Synonyms: N-HEPTYL-BETA-D-GLC;N-HEPTYL-BETA-D-GLUCOPYRANOSIDE;HEPTYL-BETA-D-GLUCOPYRANOSIDE;Heptyl--D-glucoside 150 mM Solution;N-HEPTYL B-D-GLUCOPYRANOSIDE;.beta.-D-Glucopyranoside, heptyl;n-heptyl β-d-glucopyranoside;Heptylb-D-glucopyranoside
• CAS NO: 78617-12-6
• Molecular Formula: C₁₃H₂₆O₆
• Molecular Weight: 278.34
• EINECS: 1533716-785-6
• Product Categories: Detergents;Detergents A to ZDetergents;Non-Ionic
• Mol File: 78617-12-6.mol
• Article Data: 11

Chemical Properties

• Melting Point: 74-75℃
• Boiling Point: 443.1 °C at 760 mmHg
• Flash Point: 221.8 °C
• Appearance: White to Off-white/Powder
• Density: 1.21 g/cm³
• Vapor Pressure: 1.03E-09mmHg at 25°C
• Refractive Index: 1.518
• Storage Temp.: 2-8°C
• BRN: 8806
• CAS DataBase Reference: HEPTYL-BETA-D-GLUCOPYRANOSIDE(CAS DataBase Reference)
• NIST Chemistry Reference: HEPTYL-BETA-D-GLUCOPYRANOSIDE(78617-12-6)
• EPA Substance Registry System: HEPTYL-BETA-D-GLUCOPYRANOSIDE(78617-12-6)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36
• WGK Germany: 3
• F: 3-9
• Hazardous Substances Data: 78617-12-6(Hazardous Substances Data)

Usage

Uses

n-Heptyl-beta-D-glucopyranoside is useful for lipid vesicle preparation and solubilization of membrane-bound proteins.

Purification Methods

Purify the glucoside by repeated crystallisation from Me2CO which is a better solvent than EtOAc. The acetate has m 66-68.5o and [] 20D -20.5o (c 4, CHCl3) [Pigman & Richtmyer J Am Chem Soc 64 369 1942]. [Beilstein 17 IV 2936.]

InChI:InChI=1/C13H26O6/c1-2-3-4-5-6-7-18-13-12(17)11(16)10(15)9(8-14)19-13/h9-17H,2-8H2,1H3/t9-,10-,11+,12-,13-/m1/s1

Synthetic route

n-heptyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside (28245-00-3) → n-heptyl beta-D-glucopyranoside (78617-12-6)

Conditions	Yield
With sodium methylate In methanol at 20℃; for 24h;	65%
With methanol; barium methoxide
With sodium methylate In methanol Heating;
With triethylamine In methanol; water at 20℃; for 24h;

C20H32O11 → n-heptyl beta-D-glucopyranoside (78617-12-6)

Conditions	Yield
With water; triethylamine In methanol at 50℃; for 14h;	27%

D-Glucose (2280-44-6) + n-heptan1ol (111-70-6) → heptyl α-D-glucopyranoside, anhydrous + n-heptyl beta-D-glucopyranoside (78617-12-6)

Conditions	Yield
With sulfuric acid In 1,4-dioxane Yield given;	A 18% B n/a
With sulfuric acid In 1,4-dioxane Yields of byproduct given;	A 18% B n/a

n-heptan1ol (111-70-6) + 4-nitrophenyl-β-D-glucoside (2492-87-7) → n-heptyl beta-D-glucopyranoside (78617-12-6)

Conditions	Yield
With phosphate buffer; β-glucosidase at 30℃; for 20h; pH=5;	11%

β-D-glucose (492-61-5) + n-heptan1ol (111-70-6) → n-heptyl beta-D-glucopyranoside (78617-12-6)

Conditions	Yield
With almond meal In water at 50℃; for 168h; Thermodynamic data; Equilibrium constant; Enzymatic reaction;	4.57%
With almond meal cross-linked with glutaraldehyde In water at 50℃; for 168h; Equilibrium constant; Enzymatic reaction;

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) + n-heptan1ol (111-70-6) → n-heptyl beta-D-glucopyranoside (78617-12-6)

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

n-heptan1ol (111-70-6) → n-heptyl beta-D-glucopyranoside (78617-12-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 70 percent / lithium carbonate / CH2Cl2 / 16 h / 30 °C 2: 65 percent / sodium methoxide / methanol / 24 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: silver oxide; calcium sulfate / Reagens 4: Benzol 2: barium methylate; methanol View Scheme

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → n-heptyl beta-D-glucopyranoside (78617-12-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: 70 percent / lithium carbonate / CH2Cl2 / 16 h / 30 °C 2: 65 percent / sodium methoxide / methanol / 24 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: silver oxide; calcium sulfate / Reagens 4: Benzol 2: barium methylate; methanol View Scheme

β-D-glucose pentaacetate (604-69-3) → n-heptyl beta-D-glucopyranoside (78617-12-6)

Conditions	Yield
Multi-step reaction with 3 steps 1: 90 percent / glacial acetic acid; hydrobromic acid / 2 h / 30 °C 2: 70 percent / lithium carbonate / CH2Cl2 / 16 h / 30 °C 3: 65 percent / sodium methoxide / methanol / 24 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: SnCl4; molecular sieves 4 Angstroem / CH2Cl2 / 1 h / 20 °C 2: NaOMe / methanol / Heating View Scheme

n-heptan1ol (111-70-6) + Sucrose (57-50-1) → n-heptyl beta-D-glucopyranoside (78617-12-6)

Conditions	Yield
With cellobiose; α-glucose-1-phosphate; cellobiose phosphorylase from Clostridium thermocellum YM4; sucrose phosphorylase from Pseudomonas saccharophilia In phosphate buffer at 40℃; for 20h; pH=7.0;

(2R,3S,4S,5R,6R)-2-Hydroxymethyl-6-nonyloxy-tetrahydro-pyran-3,4,5-triol (69984-73-2) → n-heptyl beta-D-glucopyranoside (78617-12-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: water / 50 °C / Enzymatic reaction 2: almond meal cross-linked with glutaraldehyde / water / 168 h / 50 °C / Enzymatic reaction View Scheme
Multi-step reaction with 2 steps 1: almond meal / water / 168 h / 50 °C 2: almond meal / water / 168 h / 50 °C / Enzymatic reaction View Scheme

n-butyl β-D-glucopyranoside (5391-18-4, 25320-93-8, 39824-09-4, 95531-15-0, 143289-25-2, 146453-36-3, 148347-27-7) → n-heptyl beta-D-glucopyranoside (78617-12-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: water / 50 °C / Enzymatic reaction 2: almond meal cross-linked with glutaraldehyde / water / 168 h / 50 °C / Enzymatic reaction View Scheme
Multi-step reaction with 2 steps 1: almond meal / water / 168 h / 50 °C 2: almond meal / water / 168 h / 50 °C / Enzymatic reaction View Scheme

1-pentanol β-D-glucopyranoside (25320-96-1, 39824-10-7, 66957-71-9, 95531-16-1, 100297-02-7, 100297-03-8) → n-heptyl beta-D-glucopyranoside (78617-12-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: water / 50 °C / Enzymatic reaction 2: almond meal cross-linked with glutaraldehyde / water / 168 h / 50 °C / Enzymatic reaction View Scheme
Multi-step reaction with 2 steps 1: almond meal / water / 168 h / 50 °C 2: almond meal / water / 168 h / 50 °C / Enzymatic reaction View Scheme

n-hexyl-β-D-glucopyranoside (39824-11-8, 59080-45-4, 95531-17-2, 29781-79-1) → n-heptyl beta-D-glucopyranoside (78617-12-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: water / 50 °C / Enzymatic reaction 2: almond meal cross-linked with glutaraldehyde / water / 168 h / 50 °C / Enzymatic reaction View Scheme
Multi-step reaction with 2 steps 1: almond meal / water / 168 h / 50 °C 2: almond meal / water / 168 h / 50 °C / Enzymatic reaction View Scheme

n-decyl β-D-glucopyranoside (58846-77-8) → n-heptyl beta-D-glucopyranoside (78617-12-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: water / 50 °C / Enzymatic reaction 2: almond meal cross-linked with glutaraldehyde / water / 168 h / 50 °C / Enzymatic reaction View Scheme

n-heptan1ol (111-70-6) + α-D-Glucopyranoside 1-(disodium phosphate) (56401-20-8) → n-heptyl beta-D-glucopyranoside (78617-12-6)

Conditions	Yield
With cellobiose phosphorylase from Clostridium thermocellum In aq. buffer at 50℃; for 48h; pH=6.5; Enzymatic reaction;

propyl Β-D-glucopyranoside (25320-91-6, 34384-77-5, 39824-08-3, 62178-32-9, 63223-88-1, 73351-01-6, 95586-01-9, 118245-33-3, 118245-34-4) → n-heptyl beta-D-glucopyranoside (78617-12-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: almond meal / water / 168 h / 50 °C 2: almond meal / water / 168 h / 50 °C / Enzymatic reaction View Scheme

n-octyl β-D-glucopyranoside (29836-26-8) → n-heptyl beta-D-glucopyranoside (78617-12-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: almond meal / water / 168 h / 50 °C 2: almond meal / water / 168 h / 50 °C / Enzymatic reaction View Scheme

n-heptan1ol (111-70-6) + pentaacetyl-β-D-glucose → n-heptyl beta-D-glucopyranoside (78617-12-6)

Conditions	Yield
Multi-step reaction with 2 steps 1: boron trifluoride diethyl etherate / dichloromethane / 24 h / 0 - 20 °C 2: triethylamine; water / methanol / 14 h / 50 °C View Scheme

n-heptyl beta-D-glucopyranoside (78617-12-6) + phenylboronic acid (98-80-6) → heptyl β-D-glucopyranoside 4,6-phenylboronate

Conditions	Yield
at 90℃; under 0.1 Torr; for 0.25h;	99%

n-heptyl beta-D-glucopyranoside (78617-12-6) → (2R,3S,4S,5R,6R)-2-Hydroxymethyl-6-nonyloxy-tetrahydro-pyran-3,4,5-triol (69984-73-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: water / 50 °C / Enzymatic reaction 2: almond meal cross-linked with glutaraldehyde / water / 168 h / 50 °C / Enzymatic reaction View Scheme
Multi-step reaction with 2 steps 1: almond meal / water / 168 h / 50 °C 2: almond meal / water / 168 h / 50 °C / Enzymatic reaction View Scheme

n-heptyl beta-D-glucopyranoside (78617-12-6) → β-D-glucose (492-61-5) + n-heptan1ol (111-70-6)

Conditions	Yield
With water at 50℃; Equilibrium constant; Enzymatic reaction;
With almond meal In water at 50℃; for 168h; Thermodynamic data; Equilibrium constant;

n-heptyl beta-D-glucopyranoside (78617-12-6) → 1-pentanol β-D-glucopyranoside (25320-96-1, 39824-10-7, 66957-71-9, 95531-16-1, 100297-02-7, 100297-03-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: water / 50 °C / Enzymatic reaction 2: almond meal cross-linked with glutaraldehyde / water / 168 h / 50 °C / Enzymatic reaction View Scheme
Multi-step reaction with 2 steps 1: almond meal / water / 168 h / 50 °C 2: almond meal / water / 168 h / 50 °C / Enzymatic reaction View Scheme

n-heptyl beta-D-glucopyranoside (78617-12-6) → n-hexyl-β-D-glucopyranoside (39824-11-8, 59080-45-4, 95531-17-2, 29781-79-1)

Conditions	Yield
Multi-step reaction with 2 steps 1: water / 50 °C / Enzymatic reaction 2: almond meal cross-linked with glutaraldehyde / water / 168 h / 50 °C / Enzymatic reaction View Scheme
Multi-step reaction with 2 steps 1: almond meal / water / 168 h / 50 °C 2: almond meal / water / 168 h / 50 °C / Enzymatic reaction View Scheme

n-heptyl beta-D-glucopyranoside (78617-12-6) → n-decyl β-D-glucopyranoside (58846-77-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: water / 50 °C / Enzymatic reaction 2: almond meal cross-linked with glutaraldehyde / water / 168 h / 50 °C / Enzymatic reaction View Scheme

n-heptyl beta-D-glucopyranoside (78617-12-6) → propyl Β-D-glucopyranoside (25320-91-6, 34384-77-5, 39824-08-3, 62178-32-9, 63223-88-1, 73351-01-6, 95586-01-9, 118245-33-3, 118245-34-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: almond meal / water / 168 h / 50 °C 2: almond meal / water / 168 h / 50 °C / Enzymatic reaction View Scheme

n-heptyl beta-D-glucopyranoside (78617-12-6) → n-butyl β-D-glucopyranoside (5391-18-4, 25320-93-8, 39824-09-4, 95531-15-0, 143289-25-2, 146453-36-3, 148347-27-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: almond meal / water / 168 h / 50 °C 2: almond meal / water / 168 h / 50 °C / Enzymatic reaction View Scheme

n-heptyl beta-D-glucopyranoside (78617-12-6) → n-octyl β-D-glucopyranoside (29836-26-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: almond meal / water / 168 h / 50 °C 2: almond meal / water / 168 h / 50 °C / Enzymatic reaction View Scheme

n-heptyl beta-D-glucopyranoside (78617-12-6) → D-glucose (50-99-7) + n-heptan1ol (111-70-6)

Conditions	Yield
With recombinant Solanum torvum GH3 β-glucosidase with a polyhistidine tag at 37℃; pH=5; Enzymatic reaction;

Upstream product

• 28245-00-3 n-heptyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside 
• 2280-44-6 D-Glucose 
• 111-70-6 n-heptan1ol 
• 2492-87-7 4-nitrophenyl-β-D-glucoside 
• 572-09-8 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide 
• 604-69-3 β-D-glucose pentaacetate 
• 57-50-1 Sucrose 
• 69984-73-2 (2R,3S,4S,5R,6R)-2-Hydroxymethyl-6-nonyloxy-tetrahydro-pyran-3,4,5-triol 
• 492-61-5 β-D-glucose 
• 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 
• 58846-77-8 n-decyl β-D-glucopyranoside 
• 56401-20-8 α-D-Glucopyranoside 1-(disodium phosphate) 

Downstream Products

• 69984-73-2 (2R,3S,4S,5R,6R)-2-Hydroxymethyl-6-nonyloxy-tetrahydro-pyran-3,4,5-triol 
• 492-61-5 β-D-glucose 
• 111-70-6 n-heptan1ol 
• 25320-96-1 O-n-pentyl β-D-glucopyranoside 
• 39824-11-8 n-hexyl-β-D-glucopyranoside 
• 58846-77-8 n-decyl β-D-glucopyranoside 
• 25320-91-6 propyl β-D-glucopyranoside 
• 5391-18-4 n-butyl β-D-glucopyranoside 
• 29836-26-8 n-octyl β-D-glucopyranoside 
• 50-99-7 D-glucose 

Relevant articles and documents

Highly β-Selective Glycosylation Reactions for the Synthesis of ω-Functionalized Alkyl β-Maltoside as a Co-crystallizing Detergent

Abstract: Methods have been reported for the preparation of ω-functionalized alkyl maltoside and glycoside detergents via a simple and inexpensive synthetic route. The key step was stannic chloride-mediated glycosylation of long-chain alcohols or thiols with maltose octaacetate at 0 or –10°C, respectively, within a very short time (isolated yield 17–44%), which provided more than 98% β-selectivity.

Significantly Improved Equilibrium Yield of Long-Chain Alkyl Glucosides via Reverse Hydrolysis in a Water-Poor System Using Cross-Linked Almond Meal as a Cheap and Robust Biocatalyst

An array of ten β-D-glucopyranosides with varied alkyl chain lengths were enzymatically synthesized. It was found that for longer alkyl chains a lower initial rate and final yield of glucoside was obtained except for methyl glucoside because of the severe toxicity of methanol to the enzyme. From a thermodynamics point of view, the equilibrium constant and Gibbs free energy variation of the glucoside syntheses were systematically investigated. To improve the final yields of the glucosides containing long alkyl chains the equilibrium of the enzymatic glucoside synthesis was altered. The equilibrium yield of decyl β-D-glucoside increased from 1.9% to 6.1% when the water content was reduced from 10% to 5% (v/v) using tert-butanol as a cosolvent and 0.10 mol/L of glucose as a substrate. As for the other longer alkyl chain glucosides, heptyl β-D-glucoside was found to have significant surface activity as well.

POLYMER STABILIZER

A polymer stabilizer comprising the following alkoxy compound: the alkoxy compound: a compound obtained by alkoxylating at least one hydroxyl group contained in a compound of the following formula (1) containing one formyl group or carbonyl group and (n?1) hydroxyl groups in the molecule with an alkyl group having 1 to 12 carbon atoms: [in-line-formulae]CnH2nOn??(1)[/in-line-formulae] (wherein, n represents an integer of 3 or more).