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CAS Number: 479-98-1Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:207-540-8
Nikkaji Web:J22.117A
Beilstein Number:0050340
XlogP3-AA:-3.00 (est)
Molecular Weight:346.33314000
Formula:C15 H22 O9
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
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Pubchem Patents:Search
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 669.02 °C. @ 760.00 mm Hg (est)
Flash Point: 677.00 °F. TCC ( 358.40 °C. ) (est)
logP (o/w): -4.103 (est)
Soluble in:
 water, 3.56E+05 mg/L @ 20 °C (exp)
 water, 1e+006 mg/L @ 25 °C (est)
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
Cosmetic Information:
None found
Alfa Biotechnology
For experimental / research use only.
Aucubin 98%
BOC Sciences
For experimental / research use only.
For experimental / research use only.
For experimental / research use only.
Aucubin (HPLC) ≥99%
Glentham Life Sciences
Santa Cruz Biotechnology
For experimental / research use only.
Aucubin ≥99%
For experimental / research use only.
analytical standard
Safety Information:
Hazards identification
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
Safety in Use Information:
natural substances and extractives
Recommendation for aucubin usage levels up to:
 not for fragrance use.
Recommendation for aucubin flavor usage levels up to:
 not for flavor use.
Safety References:
EPI System: View
AIDS Citations:Search
Cancer Citations:Search
Toxicology Citations:Search
EPA ACToR:Toxicology Data
EPA Substance Registry Services (SRS):Registry
Laboratory Chemical Safety Summary :91458
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):91458
Pubchem (sid):135048508
Other Information:
(IUPAC):Atomic Weights of the Elements 2011 (pdf)
Videos:The Periodic Table of Videos
tgsc:Atomic Weights use for this web site
(IUPAC):Periodic Table of the Elements
KEGG (GenomeNet):C09771
HMDB (The Human Metabolome Database):HMDB36562
VCF-Online:VCF Volatile Compounds in Food
Potential Blenders and core components note
None Found
Potential Uses:
None Found
Occurrence (nature, food, other):note
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 verbena plant
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PubMed:[Chemical constituents of Eucommia ulmoides].
PubMed:Aucubin promotes neurite outgrowth in neural stem cells and axonal regeneration in sciatic nerves.
PubMed:LC/MS/MS determination and pharmacokinetic studies of six compounds in rat plasma following oral administration of the single and combined extracts of Eucommia ulmoides and Dipsacus asperoides.
PubMed:Development and validation of high liquid performance chromatography-tandem mass spectrometry method for simultaneous determination of geniposidic acid and aucubin in rat plasma for pharmacokinetic study after oral administration of Du-zhong tea extract.
PubMed:The Effects of Plantago major on the Activation of the Neutrophil Respiratory Burst.
PubMed:Eucommia ulmoides cortex, geniposide and aucubin regulate lipotoxicity through the inhibition of lysosomal BAX.
PubMed:[Absorption and pharmacokinetics of radix rehmanniae in rats].
PubMed:Eucommia ulmoides Oliver extract, aucubin, and geniposide enhance lysosomal activity to regulate ER stress and hepatic lipid accumulation.
PubMed:Do fungivores trigger the transfer of protective metabolites from host plants to arbuscular mycorrhizal hyphae?
PubMed:In vivo anti-inflammatory and anti-ulcerogenic activities of extracts from wild growing and in vitro plants of Castilleja tenuiflora Benth. (Orobanchaceae).
PubMed:Incorporation of an introduced weed into the diet of a native butterfly: consequences for preference, performance and chemical defense.
PubMed:Anti-inflammatory activity of iridoids and verbascoside isolated from Castilleja tenuiflora.
PubMed:Host dependent iridoid glycoside sequestration patterns in Cionus hortulanus.
PubMed:Determination of phenylethanoid glycosides and iridoid glycosides from therapeutically used Plantago species by CE-MEKC.
PubMed:Role of plant β-glucosidases in the dual defense system of iridoid glycosides and their hydrolyzing enzymes in Plantago lanceolata and Plantago major.
PubMed:A proposed biosynthetic pathway of picrosides linked through the detection of biochemical intermediates in the endangered medicinal herb Picrorhiza kurroa.
PubMed:Compounds from the Fruits of the Popular European Medicinal Plant Vitex agnus-castus in Chemoprevention via NADP(H):Quinone Oxidoreductase Type 1 Induction.
PubMed:Correlation between polyphenol content and anti-inflammatory activity of Verbascum phlomoides (mullein).
PubMed:Aucubin, a naturally occurring iridoid glycoside inhibits TNF-α-induced inflammatory responses through suppression of NF-κB activation in 3T3-L1 adipocytes.
PubMed:Lewis acid catalyzed enlargement of cyclic β-alkoxyenals and one-pot synthesis of polyfunctional enoxysilanes derived from aucubin with trimethylsilyldiazomethane.
PubMed:Seasonal difference in antioxidant capacity and active compounds contents of Eucommia ulmoides oliver leaf.
PubMed:Iridoids from Bellardia trixago (L.) All.
PubMed:Polar constituents composition of endemic Sideritis italica (MILL.) GREUTER et BURTER from Central Italy.
PubMed:Filamentous fungi from Plantago lanceolata L. leaves: contribution to the pattern and stability of bioactive metabolites.
PubMed:Verbascum xanthophoeniceum-derived phenylethanoid glycosides are potent inhibitors of inflammatory chemokines in dormant and interferon-gamma-stimulated human keratinocytes.
PubMed:Synergistic effects of iridoid glycosides on the survival, development and immune response of a specialist caterpillar, Junonia coenia (Nymphalidae).
PubMed:[Enzymatic extraction and antibacterial activity of aucubin from Eucommia ulmoides leaves].
PubMed:Neuroprotective properties of aucubin in diabetic rats and diabetic encephalopathy rats.
PubMed:HPLC-APCI-MS/MS method for the determination of catalpol in rat plasma and cerebrospinal fluid: application to an in vivo pharmacokinetic study.
PubMed:The interplay between toxin-releasing β-glucosidase and plant iridoid glycosides impairs larval development in a generalist caterpillar, Grammia incorrupta (Arctiidae).
PubMed:Phytochemical composition of polar fraction of Stachys germanica L. subsp. salviifolia (Ten.) Gams, a typical plant of Majella National Park.
PubMed:Diet quality can play a critical role in defense efficacy against parasitoids and pathogens in the Glanville fritillary (Melitaea cinxia).
PubMed:[Iridoid glycosides from buds of Jasminum officinale L. var. grandiflorum].
PubMed:Plant community diversity influences allocation to direct chemical defence in Plantago lanceolata.
PubMed:A rapid and sensitive determination of aucubin in rat plasma by liquid chromatography-tandem mass spectrometry and its pharmacokinetic application.
PubMed:Phytochemical analysis of Plantago sempervirens from Majella National Park.
PubMed:A Validated HPTLC-Densitometric Method for Assay of Aucubin in Vitexagnus-castusL.
PubMed:Antiinflammatory activities of Hungarian Stachys species and their iridoids.
PubMed:Allergy-preventive effects of chlorogenic acid and iridoid derivatives from flower buds of Lonicera japonica.
PubMed:Protective effects of aucubin on H₂O₂-induced apoptosis in PC12 cells.
PubMed:Differential performance of a specialist and two generalist herbivores and their parasitoids on Plantago lanceolata.
PubMed:In vitro cytotoxic activity and structure activity relationships of iridoid glucosides derived from Veronica species.
PubMed:Effect of high relative humidity on dried Plantago lanceolata L. leaves during long-term storage: effects on chemical composition, colour and microbiological quality.
PubMed:[The 14 plants in Issenheim's altarpiece. An updated pharmaco-chemical approach].
PubMed:Iridoid content and biological activities of Veronica cuneifolia subsp. cuneifolia and V. cymbalaria.
PubMed:A comparison of sample preparation techniques for quantifying iridoid glycosides sequestered by lepidopteran larvae.
PubMed:[Bio-activity evaluation of Qinlian Siwu decoction on inhibiting mice uterine contraction in vitro and its components analysis].
PubMed:Cholinesterase inhibitory and antioxidant properties of Verbascum mucronatum Lam. and its secondary metabolites.
PubMed:Lavandulifolioside B: a new phenylethanoid glycoside from the aerial parts of Stachys lavandulifolia Vahl.
PubMed:Sonication-assisted Agrobacterium rhizogenes-mediated transformation of Verbascum xanthophoeniceum Griseb. for bioactive metabolite accumulation.
PubMed:Aucubin modulates Bcl-2 family proteins expression and inhibits caspases cascade in H₂O₂-induced PC12 cells.
PubMed:[Studies on the chemical constituents of Buddleja albiflora (II)].
PubMed:Influence of iridoid glycoside containing host plants on midgut β-glucosidase activity in a polyphagous caterpillar, Spilosoma virginica Fabricius (Arctiidae).
PubMed:Antiprotozoal activity of Melampyrum arvense and its metabolites.
PubMed:Bioassay-guided isolation of anti-inflammatory, antinociceptive and wound healer glycosides from the flowers of Verbascum mucronatum Lam.
PubMed:A novel series of cytotoxic iridoid glucosides derived from aucubin: design, synthesis and structure-activity relationships.
PubMed:Sequestration of glucosinolates and iridoid glucosides in sawfly species of the genus Athalia and their role in defense against ants.
PubMed:Screening of common Plantago species in Hungary for bioactive molecules and antioxidant activity.
PubMed:[Hairy root culture optimization and aucubin medical composition production of Eucommia ulmoides].
PubMed:X-ray crystal structure of iridoid glucoside aucubin and its aglycone.
PubMed:Quantitation of catalpol in rat plasma by liquid chromatography/electrospray ionization tandem mass spectrometry and its pharmacokinetic study.
PubMed:Elucidation of anti-inflammatory potencies of Eucommia ulmoides bark and Plantago asiatica seeds.
PubMed:A new iridoid glycoside from Scrophularia ningpoensis.
PubMed:The effects of arbuscular mycorrhizal fungi on direct and indirect defense metabolites of Plantago lanceolata L.
PubMed:The genome-wide expression profile of Scrophularia ningpoensis-treated thapsigargin-stimulated U-87MG cells.
PubMed:Study of chemical composition and antimicrobial activity of leaves and roots of Scrophularia ningpoensis.
PubMed:Arbuscular mycorrhizal fungal species suppress inducible plant responses and alter defensive strategies following herbivory.
PubMed:Extraction of aucubin from seeds of Eucommia ulmoides Oliv. using supercritical carbon dioxide.
PubMed:Antihepatotoxic activity and chemical constituents of Buddleja asiatica Lour.
PubMed:Iridoids from Euphrasia genargentea, a rare Sardinian endemism.
PubMed:Chemical defense, mycorrhizal colonization and growth responses in Plantago lanceolata L.
PubMed:Aucubin prevents loss of hippocampal neurons and regulates antioxidative activity in diabetic encephalopathy rats.
PubMed:A validation protocol for the HPTLC standardization of herbal products: application to the determination of acteoside in leaves of Plantago palmata Hook. f.s.
PubMed:Inhibitory Potencies of Several Iridoids on Cyclooxygenase-1, Cyclooxygnase-2 Enzymes Activities, Tumor Necrosis factor-α and Nitric Oxide Production In Vitro.
PubMed:A potential agent for treating non-small cell lung cancer.
PubMed:Cytotoxic activities of Stachys species.
PubMed:Oviposition cues for a specialist butterfly--plant chemistry and size.
PubMed:Phytochemistry and molecular systematics of Triaenophora rupestris and Oreosolen wattii (Scrophulariaceae).
PubMed:Neuroprotection of aucubin in primary diabetic encephalopathy.
PubMed:Antiproliferative activity of aucubin is through cell cycle arrest and apoptosis in human non-small cell lung cancer A549 cells.
PubMed:Gynecological efficacy and chemical investigation of Vitex agnus-castus L. fruits growing in Egypt.
PubMed:[Research advances in pharmacology of aucubin and aucubigenin].
PubMed:[Experimental studies on compound Duzhong Jiangya prescription by semi-bionic extraction].
PubMed:Antioxidant and pancreas-protective effect of aucubin on rats with streptozotocin-induced diabetes.
PubMed:Effects of aucubin on the healing of oral wounds.
PubMed:The experimental study of Cortex Eucommiae on meridian tropsim: the distribution study of aucubin in rat tissues.
PubMed:Phenylethanoids, iridoids and a spirostanol saponin from Veronica turrilliana.
PubMed:Antispasmodic activity of an extract from Plantago lanceolata L. and some isolated compounds.
PubMed:Regioselective and stereospecific amination of iridoids: conversion of aucubin into aminoside antibiotic analogues.
PubMed:Synthesis and cytotoxicity of a novel iridoid glucoside derived from aucubin.
PubMed:Bioassay-guided isolation of anti-inflammatory and antinociceptive glycoterpenoids from the flowers of Verbascum lasianthum Boiss. ex Bentham.
PubMed:Occurrence of iridoid glycosides in in vitro cultures and intact plants of Scrophularia nodosa L.
PubMed:Monoterpenoids from Stachys glutinosa L.
PubMed:Taxonomical markers in two endemic plants of Sardinia: Verbascum conocarpum and Scrophularia trifoliata.
PubMed:[Study on the chemical constituents of Buddleja purdomii].
PubMed:Chemotaxonomy of Veroniceae and its allies in the Plantaginaceae.
PubMed:Antioxidant activity of Plantago bellardii All.
PubMed:On-line identification of unstable iridoids from Jamesbrittenia fodina by HPLC-MS and HPLC-NMR.
PubMed:Inhibitory effect of Aucubin isolated from Eucommia ulmoides against UVB-induced matrix metalloproteinase-1 production in human skin fibroblasts.
PubMed:Iridoids as DNA topoisomerase I poisons.
PubMed:Protective effects of aucubin isolated from Eucommia ulmoides against UVB-induced oxidative stress in human skin fibroblasts.
PubMed:Chemotaxonomic markers in Digitalideae (Plantaginaceae).
PubMed:[Study on optimizing the analysis condition for active compound in Eucommia olive].
PubMed:Anti-protozoal and plasmodial FabI enzyme inhibiting metabolites of Scrophularia lepidota roots.
PubMed:Patterns of iridoid glycoside production and induction in Plantago lanceolata and the importance of plant age.
PubMed:Anti-inflammatory activity of aucubin by inhibition of tumor necrosis factor-alpha production in RAW 264.7 cells.
PubMed:Iridoid glucosides of Paederota lutea and the relationships between Paederota and Veronica.
PubMed:Earthworms and litter distribution affect plant-defensive chemistry.
PubMed:Plant chemical defense against herbivores and pathogens: generalized defense or trade-offs?
PubMed:Determination of aucubin and catalpol in Plantago species by micellar electrokinetic chromatography.
PubMed:Effects of Eucommiae Cortex on osteoblast-like cell proliferation and osteoclast inhibition.
PubMed:Aragoside and iridoid glucosides from Aragoa cundinamarcensis.
PubMed:Iridoid glucosides from Veronica pectinata var. glandulosa.
PubMed:Immunomodulatory activities of flavonoids, monoterpenoids, triterpenoids, iridoid glycosides and phenolic compounds of Plantago species.
PubMed:Glucosides from Vitex agnus-castus.
PubMed:Iridoid and bisiridoid glycosides from Globularia cordifolia.
PubMed:Determination of iridoid glycosides in larvae and adults of butterfly Melitaea cinxia by partial filling micellar electrokinetic capillary chromatography-electrospray ionisation mass spectrometry.
PubMed:Effect of iridoid glycoside content on oviposition host plant choice and parasitism in a specialist herbivore.
PubMed:Antileukemic activity of selected natural products in Taiwan.
PubMed:Iridoids from Globularia dumulosa.
PubMed:[Development of healthy beverage from Eucommla ulmoides foliage].
PubMed:Systemic, genotype-specific induction of two herbivore-deterrent iridoid glycosides in Plantago lanceolata L. in response to fungal infection by Diaporthe adunca (Rob.) Niessel.
PubMed:Iridoid glucosides from Veronica hederifolia.
PubMed:Inhibition of TNF-alpha and IL-6 production by Aucubin through blockade of NF-kappaB activation RBL-2H3 mast cells.
PubMed:Phenylethanoid and iridoid glycosides from Veronica persica.
PubMed:Changes in the concentrations of bioactive compounds in plantain leaves.
PubMed:Iridoid patterns of genus Plantago L. and their systematic significance.
PubMed:Determination of iridoid glycosides by micellar electrokinetic capillary chromatography-mass spectrometry with use of the partial filling technique.
PubMed:Studies on the possible mechanisms of protective activity against alpha-amanitin poisoning by aucubin.
PubMed:Selective sequestration of iridoid glycosides from their host plants in Longitarsus flea beetles.
PubMed:Iridoid glycosides from Globularia trichosantha.
PubMed:Chemotaxonomy of Plantago. Iridoid glucosides and caffeoyl phenylethanoid glycosides.
PubMed:An iridoid glucoside from Euphrasia pectinata.
PubMed:Effects of some iridoids from plant origin on arachidonic acid metabolism in cellular systems.
PubMed:Aquaticol, a bis-sesquiterpene and iridoid glucosides from Veronica anagallis-aquatica.
PubMed:Mechanism of covalent adduct formation of aucubin to proteins.
PubMed:The promoting effect of eucommiol from Eucommiae cortex on collagen synthesis.
PubMed:Extraction of iridoid glycosides and their determination by micellar electrokinetic capillary chromatography.
PubMed:Iridoids from plantago lagopus.
PubMed:Enzymatic activation of oleuropein: a protein crosslinker used as a chemical defense in the privet tree.
PubMed:Improvement in the turnover rate of the stratum corneum in false aged model rats by the administration of geniposidic acid in Eucommia ulmoides Oliver Leaf.
PubMed:Liver-protective activities of aucubin derived from traditional oriental medicine.
PubMed:Efficient conversion of aucubin into 6-epi-aucubin
PubMed:Verbaspinoside, a new iridoid glycoside from Verbascum spinosum.
PubMed:The promoting effects of geniposidic acid and aucubin in Eucommia ulmoides Oliver leaves on collagen synthesis.
PubMed:A new eremophilane sesquiterpenoid and a new iridoid from Pedicularis striata subsp. arachnoides.
PubMed:Neuritogenic effect of natural iridoid compounds on PC12h cells and its possible relation to signaling protein kinases.
PubMed:Inhibition of P-450 by aucubin: is the biological activity of aucubin due to its glutaraldehyde-like aglycone?
PubMed:Verbascoside derivatives and iridoid glycosides from Penstemon crandallii.
PubMed:Iridoid glucosides from Penstemon ovatus.
PubMed:In vitro antispasmodic activity of peracetylated penstemonoside, aucubin and catalpol.
PubMed:Promotion of neuronal differentiation of PC12h cells by natural lignans and iridoids.
PubMed:Structural considerations on the iridoids as anti-inflammatory agents.
PubMed:Iridoid glycosides ofChelone glabra (Scrophulariaceae) and their sequestration by larvae of a sawfly,Tenthredo grandis (Tenthredinidae).
PubMed:Karsoside and scropolioside D, two new iridoid glycosides from Scrophularia ilwensis.
PubMed:The effect of nutrients and enriched CO$_2$ environments on production of carbon-based allelochemicals in Plantago: a test of the carbon/nutrient balance hypothesis.
PubMed:Chemical variation within and between individuals ofPlantago lanceolata (Plantaginaceae).
PubMed:Fate of iridoid glycosides in different life stages of the Buckeye,Junonia coenia (Lepidoptera: Nymphalidae).
PubMed:[Determination of aucubin in Plantago asiatica L., P. major L. and P. depressa Willd. by HPLC].
PubMed:Pharmacokinetic study of an iridoid glucoside: aucubin.
PubMed:Host plant utilization and iridoid glycoside sequestration byEuphydryas anicia (Lepidoptera: Nymphalidae).
PubMed:Iridoid glycosides as oviposition stimulants for the buckeye butterfly,Junonia coenia (Nymphalidae).
PubMed:Response of generalist and specialist insects to qualitative allelochemical variation.
PubMed:Euphydryas anicia (Lepidoptera: Nymphalidae) utilization of iridoid glycosides fromCastilleja andBesseya (Scrophulariaceae) host plants.
PubMed:Aucubin: potential antidote for alpha-amanitin poisoning.
PubMed:Protective activities of aucubin against carbon tetrachloride-induced liver damage in mice.
PubMed:Iridoid glucosides of Melampyrum laxum.
PubMed:[Methods of aucubin detection].
PubMed:[Localization and displacement of the glycoside aucubin in the plant].
PubMed:[Occurrence of aucubin in some species of the Scrophulariaceae family].
PubMed:[Determination of aucubin in some species of the plants from family Scrophulariaceae].
PubMed:[Aucubin content in medicinal plants from Veronica species].
PubMed:[Quantitative determination of aucubin in Eucommiaceae].
PubMed:The preparation and properties of aucubin, asperuloside and some related glycosides.
Aucubin is a monoterpenoid based compound. Aucubin, like all iridoids, has a cyclopentan-[C]-pyran skeleton. Iridoids can consist of ten, nine, or rarely eight carbons in which C11 is more frequently missing than C10. Aucubin has 10 carbons with the C11 carbon missing. The stereochemical configurations at C5 and C9 lead to cis fused rings, which are common to all iridoids containing carbocylclic- or seco-skeleton in non-rearranged form. Oxidative cleavage at C7-C8 bond affords secoiridoids. The last steps in the biosynthesis of iridoids usually consist of O-glycosylation and O-alkylation. Aucubin, a glycoside iridoid, has an O-linked glucose moiety.; Aucubin is an iridoid glycoside. Iridoids are commonly found in plants and function as defensive compounds. Irioids decrease the growth rates of many generalist herbivores. Aucubin is found in the leaves of Aucuba japonica (Cornaceae), Eucommia ulmoides (Eucommiaceae), and Plantago asiatic (Plantaginaceae), etc, plants used in traditional Chinese and folk medicine. Aucubin was found to protect against liver damage induced by carbon tetrachloride or alpha-amanitin in mice and rats when 80 mg/kg was dosed intraperitoneally.; Geranyl pyrophosphate is the precursor for iridoids. Geranyl phosphate is generated through the mevalonate pathway or the methylerythritol phosphate pathway. The initial steps of the pathway involve the fusion of three molecules of acetyl-CoA to produce the C6 compound 3-hydroxy-3-methylglutaryl-CoA (HMG-CoA). HMG-CoA is then reduced in two steps by the enzyme HMG-CoA reductase. The resulting mevalonate is then sequentially phosphorylated by two separate kinases, mevalonate kinase and phosphomevalonate kinase, to form 5-pyrophosphomevalonate. Phosphosphomevalonate decarboxylase through a concerted decarboxylation reaction affords isopentenyl pyrophosphate (IPP). IPP is the basic C5 building block that is added to prenyl phosphate cosubstrates to form longer chains. IPP is isomerized to the allylic ester dimethylallyl pyrophosphate (DMAPP) by IPP isomerase. Through a multistep process, including the dephosphorylation DMAPP, IPP and DMAPP are combinded to from the C10 compound geranyl pyrophosphate (GPP). Geranyl pyrophosphate is a major branch point for terpenoid synthesis.; The cyclizaton reaction to form the iridoid pyrane ring may result from one of two routes: route 1 - a hydride nucleophillic attack on C1 will lead to 1-O-carbonyl atom attack on C3, yielding the lactone ring; route 2 - loss of proton from carbon 4 leads to the formation of a double bond C3-C4; consequently the 3-0-carbonyl atom will attach to C1.
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