479-98-1

Basic information

• Product Name: Aucubin
• Synonyms: AUCUBIN;AUCUBOSIDE;B-D-GLUCOPYRANOSIDE, (1S,4AR,5S,7AS)-1,4A,5,7A-TETRAHYDRO-5-HYDROXY-7-(HYDROXYMETHYL)CYCLOPENTA[C]PYRAN-1-YL;RHINANTHIN;1,4a,5,7a-tetrahydro-5-hydroxy-7-(hydroxymethyl)cyclopenta[c]pyran-1-yl-beta-D-glucopyranoside;[1S-(1alpha,4aalpha,5alpha,7aalpha)]-1,4a,5,7a-tetrahydro-5-hydroxy-7-(hydroxymethyl)cyclopenta[c]pyran-1-yl-beta-D-glucopyranoside;(2S,3R,4S,5S,6R)-2-{[(1S,4aR,5S,7aS)-5-hydroxy-7-(hydroxyMethyl)-1H,4aH,5H,7aH-cyclopenta[c]pyran-1-yl]oxy}-6-(hydroxyMethyl)oxane-3,4,5-triol;Aucubosid
• CAS NO: 479-98-1
• Molecular Formula: C15H22O9
• Molecular Weight: 346.33
• EINECS: 207-540-8
• Product Categories: chemical reagent;pharmaceutical intermediate;phytochemical;reference standards from Chinese medicinal herbs (TCM).;standardized herbal extract;Iridoids;Natural Terpene StandardsChemical Class;OtherChemical Class;Oxygen containingChemical Class;Polyhydroxy compoundsMore...Close...;A;Alcohols;Alphabetic;AR to AZChromatography;Heterocyclics;Life Sciences Standards;Natural Compounds;Natural CompoundsChemical Class;Cytokine signaling
• Mol File: 479-98-1.mol
• Article Data: 7

Chemical Properties

• Melting Point: 181°
• Boiling Point: 669.025 °C at 760 mmHg
• Flash Point: 358.414 °C
• Appearance: white crystal
• Density: 1.614 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.66
• Storage Temp.: 2-8°C
• PKA: 12.80±0.70(Predicted)
• BRN: 50340
• CAS DataBase Reference: Aucubin(CAS DataBase Reference)
• NIST Chemistry Reference: Aucubin(479-98-1)
• EPA Substance Registry System: Aucubin(479-98-1)

Safety Data

• Statements: 22
• Safety Statements: 22-45
• WGK Germany: 3
• F: 10-23
• Hazardous Substances Data: 479-98-1(Hazardous Substances Data)

Usage

Chemical Properties

Aucubin, bitter in taste, easily soluble in water, ethanol, methanol, insoluble in chloroform, ether, petroleum ether and other solvents. It is a kind of iridoid compound that widely exists in many plant species in nature.

Mechanism of action

Aucubin can be used to clear dampness and heat, facilitate urination, relieving pain, reduce blood pressure and protecting liver. It can promote the regeneration of stem cells, significantly inhibit the replication of hepatitis B virus DNA.

InChI:InChI=1/C15H22O9/c16-4-6-3-8(18)7-1-2-22-14(10(6)7)24-15-13(21)12(20)11(19)9(5-17)23-15/h1-3,7-21H,4-5H2/t7?,8?,9-,10?,11-,12+,13-,14?,15+/m1/s1

Synthetic route

→ aucubin (479-98-1)

hexa-O-acetyl-aucubin (11044-25-0) → 6-O-acetyl-aucubin (135743-80-5) + aucubin (479-98-1)

Conditions	Yield
With potassium cyanide In methanol; dichloromethane at 20℃; for 7h;	A 45% B 519 mg

penta-O-acetyl-6-chetoaucubin (82504-05-0) → 6-epi-aucubin (82535-77-1) + aucubin (479-98-1)

Conditions	Yield
With sodium tetrahydroborate In ethanol at 95℃; for 0.166667h; Yield given. Yields of byproduct given;

2'-O-benzoylaucubin → aucubin (479-98-1)

Conditions	Yield
With sodium hydroxide Ambient temperature;	0.2 g

hexa-O-acetyl-aucubin (11044-25-0) → aucubin (479-98-1)

Conditions	Yield
With sodium methylate In methanol
Multi-step reaction with 3 steps 1: aq H2SO4 / dioxane / 24 h / 40 °C 2: Jones-reagent / acetone / 0.17 h / 0 - 5 °C 3: NaBH4 / ethanol / 0.17 h / 95 °C View Scheme

acuminatuside → Methyl ferulate (2309-07-1) + aucubin (479-98-1)

Conditions	Yield
With sodium methylate In methanol at 22℃; for 1h;

aucubin (479-98-1) → tetrahydro-aucubin

Conditions	Yield
With hydrogen; palladium on activated charcoal In ethanol	100%

aucubin (479-98-1) + 2,2-dimethoxy-propane (77-76-9) → 10β-4',6'-O-isopropylidene-3,4,7,8-tetrahydroaucubin

Conditions	Yield
Stage #1: aucubin; 2,2-dimethoxy-propane With pyridinium p-toluenesulfonate; copper(II) sulfate In acetone at 0 - 5℃; for 96h; Substitution; Stage #2: With hydrogen; triethylamine; palladium on activated charcoal In methanol for 24h; Hydrogenation; Stage #3: With acetic acid In tetrahydrofuran for 48h; Hydrolysis;	90%

pivaloyl chloride (3282-30-2) + aucubin (479-98-1) → (1S,4aR,5S,7aS)-5-(2,2-dimethyl-1-oxopropoxy)-7-[(2,2-dimethyl-1-oxopropoxy)methyl]-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl 2,3,4,6-tetrakis-O-(2,2-dimethyl-1-oxopropyl)-β-D-glucopyranoside (318267-52-6)

Conditions	Yield
With pyridine; dmap at 20℃; for 168000h; Acylation;	90%
With pyr	76%
With pyridine; dmap In dichloromethane at 20℃; for 96h; Inert atmosphere;

aucubin (479-98-1) → C15H20O9

Conditions	Yield
With 4-methyl-morpholine; 6C6H15P*4CF3O3S(1-)*2Ru(2+); acetone at 65℃; for 1h; Inert atmosphere; Sealed tube;	87%

aucubin (479-98-1) → 6,10-bisdeoxyaucubin (31655-27-3) + monodeoxyaucubin (63879-67-4)

Conditions	Yield
With lithium In ammonia at -70℃; for 0.166667h;	A 10% B 80%

acetic anhydride (108-24-7) + aucubin (479-98-1) + tert-butyldimethylsilyl chloride (18162-48-6) → 6,2',3',4',6'-penta-O-acetyl-10-O-tert-butyldimethylsilylaucubin + 2',3',4'-tri-O-acetyl-6,10,6'-tri-O-tert-butyldimethylsilylaucubin + 6,2',3',4'-tetra-O-acetyl-10,6'-di-O-tert-butyldimethylsilylaucubin + 6,10,2',3',4'-penta-O-acetyl-6'-O-tert-butyldimethylsilylaucubin

Conditions	Yield
Stage #1: aucubin; tert-butyldimethylsilyl chloride With pyridine In dichloromethane at 0 - 20℃; for 1h; Stage #2: acetic anhydride With pyridine In dichloromethane at 20℃; for 24h; Further stages.;	A 1% B 16% C 63% D 1%

aucubin (479-98-1) + 2,2-dimethoxy-propane (77-76-9) → 4',6'-O-isopropylidene-aucubin (256221-84-8) + 4',6'-O-isopropylidene-10-O-(1-methyl-1-methoxyethyl)aucubin + 4',6'-O-isopropylidene-6-O-(1-methyl-1-methoxyethyl)aucubin

Conditions	Yield
With pyridinium p-toluenesulfonate; copper(II) sulfate In acetone at 0 - 5℃; for 96h; Substitution;	A 40% B n/a C n/a

acetic anhydride (108-24-7) + aucubin (479-98-1) → hexa-O-acetyl-aucubin (11044-25-0)

Conditions	Yield
With pyridine at 20℃; for 1.5h;	30%

aucubin (479-98-1) → (1S,4aR,5S,7aS)-5-Hydroxy-1-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-7-carbaldehyde

Conditions	Yield
With manganese(IV) oxide In water; acetone for 48h; Ambient temperature;	8%

aucubin (479-98-1) → (4aR)-1ξ-Hydroxy-7ξ-methyl-(4ar,7ac)-octahydro-cyclopenta[c]pyran (90646-36-9) + (4aR)-1ξ-ethoxy-7ξ-methyl-(4ar,7ac)-octahydro-cyclopenta[c]pyran (91267-40-2)

Conditions	Yield
With sulfuric acid; platinum Hydrogenation;

methanol (67-56-1) + aucubin (479-98-1) → (1S,4S,5S)-3,4-Bis-hydroxymethyl-5-((E)-2-methoxy-vinyl)-cyclopent-2-enol (139013-62-0)

Conditions	Yield
With sodium hydroxide; sodium tetrahydroborate; mercury(II) diacetate 1) MeOH, 20 min, 2) 0 - 5 deg C, 20 min; Yield given. Multistep reaction;

methanol (67-56-1) + aucubin (479-98-1) → (1S,4S,5S)-3,4-Bis-hydroxymethyl-5-((E)-2-methoxy-vinyl)-cyclopent-2-enol (139013-62-0) + (1R,2R)-3,4-Bis-hydroxymethyl-2-((E)-2-methoxy-vinyl)-cyclopent-3-enol (129715-16-8)

Conditions	Yield
With sodium tetrahydroborate; methanolate; mercury(II) diacetate 1) MeOH, 20 min, 2) 20 min; Yield given. Multistep reaction. Yields of byproduct given;

methanol (67-56-1) + aucubin (479-98-1) → (1S,4S,5S)-3,4-Bis-hydroxymethyl-5-((E)-2-methoxy-vinyl)-cyclopent-2-enol (139013-62-0) + 3,4-dihydro-3α-methoxyaucubin (129715-14-6)

Conditions	Yield
With sodium tetrahydroborate; KH2PO4 buffer; mercury(II) diacetate 1) MeOH, 20 min, 2) 20 min; Yield given. Multistep reaction. Yields of byproduct given;

Upstream product

• 127183-94-2 (8S)-(-)-Hexaacetyl-7,8-dihydro-8-hydroxyaucubin 
• 11044-25-0 hexa-O-acetyl-aucubin 
• 82504-05-0 penta-O-acetyl-6-chetoaucubin 
• 82504-04-9 Acetic acid (1S,4aR,5S,7aS)-5-hydroxy-1-((2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yloxy)-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-7-ylmethyl ester 

Downstream Products

• 2280-44-6 D-Glucose 
• 64274-28-8 aucubigenin 
• 7208-47-1 1,2,3,4,5,6-hexa-O-acetyl-D-glucitol 
• 64274-27-7 (5R)-2-methyl-5-(2-oxoethyl)cyclopent-1-ene-1-carbaldehyde 
• 111589-54-9 C₂₇H₃₀O₈ 
• 111563-50-9 Benzoic acid (2aS,3S,4S,4aR,6R,7aS,7bS)-2a,6-diethoxy-3-hydroxy-octahydro-1,7-dioxa-cyclopenta[cd]inden-4-yl ester 
• 64274-28-8 aucubigenin 
• 64274-28-8 (1R,4aR,7aS)-7-Hydroxymethyl-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-1,5-diol 

Relevant articles and documents

Efficient conversion of aucubin into 6-epi-aucubin

Selective deprotection of peracetylaucubin (3) by use of KCN led to 6- O-acetylaucubin (4), which was readily converted into 2',3',4',6',10-penta- O-benzoylaucubin (7). Configuration inversion performed on 7, using a modified Mitsunobu reaction, followed by deprotection, afforded 6-epi- aucubin (2).

Iridoids and other glucosides from Penstemon acuminatus

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Chemistry and Stereochemistry of Iridoids, XIV. - Aucubin and Scandoside from Catalpol

Aucubin (9), scandoside (10), and its methyl ester were obtained, in good yields, from catalpol (1).The absolute configurations of 9-11 were established by correlation to catalpol, whose X-ray structure has previously been determined.