479-98-1

Usage

Uses

Used in Pharmaceutical Industry:
Aucubin is used as a pharmaceutical compound for its potential therapeutic properties. Its bitter taste and solubility characteristics make it a candidate for the development of new drugs and treatments, particularly in the areas of natural medicine and herbal remedies.
Used in Cosmetics Industry:
Due to its solubility in water and alcohol-based solvents, Aucubin can be used as an active ingredient in the cosmetics industry. It may be incorporated into skincare products, hair care formulations, or other beauty products for its potential benefits to skin and hair health.
Used in Agricultural Industry:
Aucubin's presence in various plant species suggests that it may have applications in the agricultural industry. It could be used as a natural pesticide or as a component in the development of more sustainable and environmentally friendly agricultural practices.
Used in Food and Beverage Industry:
Given its bitter taste, Aucubin may find use in the food and beverage industry as a natural flavoring agent or as a component in the development of new and unique flavors for various products.

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

• 11044-25-0 hexa-O-acetyl-aucubin 
• 127183-94-2 (8S)-(-)-Hexaacetyl-7,8-dihydro-8-hydroxyaucubin 
• 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 
• 82504-05-0 penta-O-acetyl-6-chetoaucubin 

Downstream Products

• 64274-28-8 (1R,4aR,7aS)-7-Hydroxymethyl-1,4a,5,7a-tetrahydro-cyclopenta[c]pyran-1,5-diol 
• 64274-28-8 aucubigenin 
• 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 
• 7208-47-1 1,2,3,4,5,6-hexa-O-acetyl-D-glucitol 
• 2280-44-6 D-Glucose 

Relevant academic research and scientific papers

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).

Stereoselective hydrogenation and ozonolysis of iridoids. Conversion into carbocyclic nucleoside analogues

Stereoselective hydrogenation of the iridoids geniposide (9) and aucubin (19) was achieved by using the 1-methyl-1- methoxyethyl ether as a protecting group for the allylic alcohol, as it enhanced the stereoselectivity and prevented undesired hydrogenolysis. Ozonolysis of the hydrogenation product from 9, adoxoside (11), with reductive workup, afforded either a chiral lactone (25) or a chiral polyol (26), depending on the reduction conditions. Polyol 26 was subjected to protecting-group manipulation and subsequent oxidation and reductions to yield cyclopentane building blocks (29-34), which, by Mitsunobu couplings with purines, afforded carbocyclic nucleoside analogues (7, 8, and 35).

Hair dyeing by iridoid glycosides and aglycons thereof

A method of dyeing hair which comprises contacting hair with an iridoid glycoside or an aglycon thereof.

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.

A NEW IRIDOID ESTER: THE 2'-O-BENZOYLAUCUBIN

A new aucubin-type iridoid (2) which contains a benzoyl group, has been isolated from Odontites verna ssp. serotina (Scrophulariaceae).Chemical and spectroscopic data demonstrate that 2 has the structure of 2'-benzoylaucubin.