Record Information
Version1.0
Creation date2010-04-08 22:10:15 UTC
Update date2019-11-26 03:07:07 UTC
Primary IDFDB012575
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameEllagic acid
DescriptionWidely distributed in higher plants especies dicotyledons. Intestinal astringent, dietary role disputed. Nutriceutical with anticancer and antioxidation props. Ellagic acid is a Polyphenol compound found in numerous fruits and vegetables, including, raspberries; Ellagic acid is a polyphenol antioxidant found in numerous fruits and vegetables including raspberries, strawberries, cranberries, walnuts, pecans, pomegranates and other plant foods. The antiproliferative and antioxidant properties of ellagic acid have spurred preliminary research into the potential health benefits of ellagic acid consumption.; and other plant foods. It is often regarded as an antioxidant. Ellagic Acid Clinical Tests on cultured human cells also show that Ellagic acid prevents the destruction of the p53 gene by cancer cells. Additional studies suggest that one of the mechanisms by which Ellagic acid inhibits mutagenesis and carcinogenesis is by forming adducts with DNA, thus masking binding sites to be occupied by the mutagen or carcinogen.; cranberries; pecans; pomegranates; strawberries; walnuts.
CAS Number476-66-4
Structure
Thumb
Synonyms
SynonymSource
2,3,7,8-Tetrahydroxy[1]benzopyrano[5,4,3-cde][1]benzopyran-5,10-dioneChEBI
4,4',5,5',6,6'-Hexahydroxydiphenic acid 2,6,2',6'-dilactoneChEBI
Acide ellagiqueChEBI
Acido elagicoChEBI
Acidum ellagicumChEBI
Benzoaric acidChEBI
EllagsaeureChEBI
LagistaseChEBI
4,4',5,5',6,6'-Hexahydroxydiphenate 2,6,2',6'-dilactoneGenerator
BenzoarateGenerator
EllagateGenerator
Acid, benzoaricMeSH
Acid, ellagicMeSH
Alizarine yellowHMDB
ElagostasineHMDB
EleagateHMDB
Eleagic acidHMDB
Ellagic acid dihydrateHMDB
Ellagic acid hydrateHMDB
GallogenHMDB
LlagateHMDB
Llagic acidHMDB
Ellagic acidPhytoBank
2,3,7,8-Tetrahydroxy[1]benzopyrano[5,4,3-cde][1]benzopyran-5,10-dione, 9CIdb_source
Alizarin yellowdb_source
Gallogen?db_source
Kajidindb_source
Predicted Properties
PropertyValueSource
Water Solubility0.82 g/LALOGPS
logP1.59ALOGPS
logP2.32ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)5.54ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area133.52 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity70.61 m³·mol⁻¹ChemAxon
Polarizability26.34 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC14H6O8
IUPAC name6,7,13,14-tetrahydroxy-2,9-dioxatetracyclo[6.6.2.0^{4,16}.0^{11,15}]hexadeca-1(15),4,6,8(16),11,13-hexaene-3,10-dione
InChI IdentifierInChI=1S/C14H6O8/c15-5-1-3-7-8-4(14(20)22-11(7)9(5)17)2-6(16)10(18)12(8)21-13(3)19/h1-2,15-18H
InChI KeyAFSDNFLWKVMVRB-UHFFFAOYSA-N
Isomeric SMILESOC1=C(O)C2=C3C(=C1)C(=O)OC1=C3C(=CC(O)=C1O)C(=O)O2
Average Molecular Weight302.194
Monoisotopic Molecular Weight302.006267153
Classification
Description Belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassTannins
Sub ClassHydrolyzable tannins
Direct ParentHydrolyzable tannins
Alternative Parents
Substituents
  • Hydrolyzable tannin
  • Ellagic_acid
  • 7,8-dihydroxycoumarin
  • Coumarin
  • Isocoumarin
  • Benzopyran
  • 2-benzopyran
  • 1-benzopyran
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Lactone
  • Polyol
  • Organoheterocyclic compound
  • Oxacycle
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 55.64%; H 2.00%; O 42.35%DFC
Melting PointMp 360°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data366 (e 8511) (MeOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSEllagic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0uk9-0095000000-fbb3052375510a43a32eSpectrum
Predicted GC-MSEllagic acid, 4 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0100-3000090000-98c2eaf6f099a674f556Spectrum
Predicted GC-MSEllagic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-0009000000-40fcade2aa63aa93a2ae2012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0zi0-0192000000-778eac8f3ed58bcaac742012-07-25View Spectrum
MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-0zi0-0093000000-8a6cc05fc65249815e822017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0zfr-1589000000-a4f6e3a25012f7426f7d2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0a6r-0192000000-39923f8b1dd96716ea792017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-001i-0090000000-a1f823c8fd710f0476d92017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , positivesplash10-0udi-0039000000-911cfbddb0cc618af2742017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - , positivesplash10-0zfr-1589000000-a4f6e3a25012f7426f7d2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-67c5a949d6d186ed40d52015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0039000000-d2f61e8b5cdaa0f142ba2015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-0090000000-961daa97dff240069d922015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0029000000-246b5797e3aacdc8f2f22015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0059000000-cc29f1c85d471f50bb6b2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-114i-0190000000-6c3c3d5d2c468609b6122015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-9600b3c9d9dcbf3cca2a2021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0029000000-9f6b76087b40406d9ff32021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-0090000000-e7359efe114a8fa3c0e32021-09-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-49d4f264ad1b5c5b0fff2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0009000000-49d4f264ad1b5c5b0fff2021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6s-0090000000-6cad49e11cb1c2a2c0ee2021-09-23View Spectrum
NMR
TypeDescriptionView
1D NMR1H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, DMSO, experimental)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, DMSO, experimental)Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)Spectrum
ChemSpider ID4445149
ChEMBL IDCHEMBL6246
KEGG Compound IDC10788
Pubchem Compound ID5281855
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer ID417
DrugBank IDDB08846
HMDB IDHMDB02899
CRC / DFC (Dictionary of Food Compounds) IDHJC14-Y:HJC14-Y
EAFUS IDNot Available
Dr. Duke IDELLAGIC-ACID
BIGG IDNot Available
KNApSAcK IDC00011153
HET IDREF
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite ID417
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
Abortifacient50691 An agent that induces abortion, disrupting pregnancy by blocking progesterone or causing uterine contractions. Therapeutically, it's used to terminate early pregnancies, manage ectopic pregnancies, or treat miscarriages. Key medical uses include medical abortion, pregnancy termination, and menstrual regulation.DUKE
Angiotensin converting enzyme inhibitor35457 An agent that blocks the conversion of angiotensin I to angiotensin II, reducing blood pressure and fluid retention. Therapeutically, it's used to treat hypertension, heart failure, and protect kidney function in diabetes, thereby reducing the risk of cardiovascular disease and stroke.DUKE
Aldose reductase inhibitor48550 An agent that blocks the activity of aldose reductase, an enzyme involved in glucose metabolism. It reduces oxidative stress and inflammation, commonly used in managing diabetic complications, such as neuropathy, nephropathy, and retinopathy.DUKE
Anti aflatoxin35222 An agent that neutralizes or removes aflatoxins, toxic compounds produced by mold, reducing the risk of liver damage and cancer. Therapeutically, it is used to prevent aflatoxin poisoning, commonly in food safety and liver protection applications, and may have potential in cancer prevention and treatment.DUKE
Anti-anaphylactic52217 An agent that prevents or treats anaphylaxis, a severe allergic reaction. It plays a biological role in stabilizing mast cells and reducing histamine release. Therapeutically, it is used to manage allergic emergencies, with key medical applications including treatment of anaphylactic shock, asthma, and allergic rhinitis.DUKE
Anti bacterial33282 An agent that inhibits the growth of or destroys bacteria, playing a crucial role in preventing and treating infections. Therapeutically, it is used to combat bacterial infections, with key medical applications including treating pneumonia, tuberculosis, and skin infections, as well as preventing surgical site infections and sepsis.DUKE
Anti-cancer35610 An agent that inhibits the growth and proliferation of cancer cells, used to treat and manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, to reduce tumor size, prevent metastasis, and improve patient survival.DUKE
Anti cariogenic52217 An agent that prevents tooth decay, reducing bacterial acid production and plaque formation. Its biological role is to inhibit the growth of cariogenic bacteria, and its therapeutic applications include preventing dental caries and managing tooth decay. Key medical uses include toothpaste, mouthwashes, and dental varnishes to maintain oral health.DUKE
Anti-cataract52217 An agent that prevents or slows the formation of cataracts, reducing oxidative stress and inflammation in the lens of the eye, commonly used to manage age-related cataracts and other ocular disorders.DUKE
Anti-gingivitic52217 An agent that reduces gingivitis symptoms, commonly used in managing plaque, inflammation, and gum disease, promoting oral health by preventing bacterial growth and infection.DUKE
Anti glucose-tolerance-factorAn antibody that binds glucose tolerance factor (GTF), blocking its insulin-mimetic activity. It may have therapeutic applications in managing insulin resistance and diabetes, and potential medical uses in treating related metabolic disorders.DUKE
Anti HIV22587 An agent that prevents the replication of the Human Immunodeficiency Virus (HIV), used to treat and manage HIV infection and Acquired Immunodeficiency Syndrome (AIDS), reducing viral load and slowing disease progression.DUKE
Anti hyperthyroid52217 An agent that reduces thyroid hormone production, used to manage hyperthyroidism by decreasing thyroid-stimulating hormone (TSH) and thyroid hormone levels, commonly used to treat conditions such as Graves' disease and thyroid storm.DUKE
Anti-inflammatory35472 An agent that reduces inflammation, playing a biological role in suppressing immune responses and therapeutic applications in managing pain, swelling, and redness. Key medical uses include treating arthritis, allergies, and autoimmune disorders, as well as relieving symptoms of conditions such as asthma and dermatitis.DUKE
Anti-malarial33281 An agent that prevents or treats malaria, a disease caused by Plasmodium parasites. It works by targeting the parasite's life cycle, reducing symptoms and preventing transmission. Therapeutically, anti-malarials are used to treat and prevent malaria, as well as to manage related conditions such as babesiosis and toxoplasmosis.DUKE
Anti-mutagenicAn agent that interferes with the mutagenicity of a substance, preventing DNA damage and mutations. Its biological role is to protect cells from genetic alterations, and it has therapeutic applications in cancer prevention and treatment, as well as key medical uses in reducing the risk of genetic disorders and birth defects.DUKE
Anti-oxidant22586 An agent that neutralizes free radicals, reducing oxidative stress and cell damage. Its biological role involves protecting cells from harm, and it has therapeutic applications in managing chronic diseases, such as cancer, diabetes, and neurodegenerative disorders, with key medical uses including anti-aging, anti-inflammatory, and cardio protective effects.DUKE
Anti periodonticAn agent that prevents or treats periodontal disease, reducing inflammation and infection in the gums and supporting tissues of the teeth, commonly used in managing periodontitis, gingivitis, and promoting oral health.DUKE
Anti peroxidantAn agent that prevents oxygen atom and peroxide formation, reducing oxidative stress and cell damage. It plays a biological role in protecting cells from free radicals. Therapeutically, it's used to manage conditions like cancer, Alzheimer's, and atherosclerosis, with key medical applications in neuroprotection, cardiovascular health, and anti-aging.DUKE
Anti-plaqueAn agent that removes or prevents the formation of dental plaque, a biofilm of bacteria, to prevent tooth decay and gum disease, commonly used in oral care products and therapeutic applications for periodontal health.DUKE
Anti plasmodial33281 An agent that inhibits the growth of Plasmodium parasites, reducing malaria symptoms. Therapeutically, it's used to treat and prevent malaria, with key medical applications including prophylaxis and treatment of malaria infections.DUKE
Anti septic33281 An agent that prevents or reduces the growth of microorganisms, such as bacteria, fungi, or viruses, to promote wound healing and prevent infection. Therapeutically, anti septics are used to treat minor cuts, scrapes, and burns, and are commonly applied topically to reduce the risk of infection and promote tissue repair. Key medical uses include wound care, surgical site preparation, and skin infection management.DUKE
Anti-streptococcic33282 An agent that targets and combats Streptococcus bacteria, reducing infection and inflammation. Therapeutically, it is used to treat streptococcal infections, such as strep throat and skin infections, and to prevent complications like rheumatic fever.DUKE
Anti-thyroidAn agent that inhibits thyroid hormone production, used to treat hyperthyroidism by reducing thyroid hormone levels, commonly applied in managing conditions like Graves' disease.DUKE
Antitumor35610 An agent that inhibits tumor growth and proliferation, playing a crucial role in cancer treatment. Therapeutically, antitumors are used to manage various types of cancer, including chemotherapy, targeted therapy, and immunotherapy, helping to reduce tumor size, prevent metastasis, and improve patient outcomes.DUKE
Anti-viral22587 An agent that inhibits the replication of viruses, playing a crucial role in preventing and treating viral infections. Therapeutically, anti-virals are used to manage diseases such as HIV, herpes, and influenza, reducing symptoms and slowing disease progression. Key medical uses include treating viral hepatitis, respiratory syncytial virus, and COVID-19.DUKE
Anti-yeast33281 An agent that inhibits the growth of yeast, playing a role in preventing fungal infections. Therapeutically, it is used to treat conditions such as candidiasis and athlete's foot, and has applications in managing digestive issues and skin infections.DUKE
ApoptoticAn agent that stimulates programmed cell death, playing a crucial biological role in eliminating damaged or unwanted cells. It has therapeutic applications in cancer treatment, and key medical uses include inducing cell death in malignant cells, reducing tumor growth, and enhancing chemotherapy efficacy.DUKE
Astringent74783 An agent that constricts or shrinks tissues, reducing bleeding and inflammation. It plays a biological role in wound healing and has therapeutic applications in treating hemorrhoids, diarrhea, and skin irritations. Key medical uses include reducing swelling, stopping bleeding, and protecting mucous membranes, making it useful in various topical and oral preparations.DUKE
Cancer preventive35610 An agent that inhibits the development and progression of cancer, reducing tumor formation and growth. It plays a biological role in blocking carcinogenic pathways, and has therapeutic applications in chemoprevention. Key medical uses include reducing the risk of cancer in high-risk individuals and preventing cancer recurrence.DUKE
Candida-secreted-aspartyl-proteinase inhibitor35222 An agent that blocks Candida-secreted aspartyl proteinase, reducing fungal virulence and inflammation. Therapeutically, it may be used to treat candidiasis, particularly in immunocompromised patients, and has potential applications in managing oral and vaginal yeast infections.DUKE
Cytotoxic52209 An agent that kills or damages cells, playing a biological role in immune responses and therapeutic applications in cancer treatment. Key medical uses include chemotherapy, targeting and destroying cancer cells, and treating certain autoimmune diseases by eliminating harmful cells.DUKE
Deiodinase inhibitor23924 An agent that blocks the activity of deiodinases, enzymes involved in thyroid hormone regulation. It reduces thyroid hormone conversion, commonly used in managing thyroid disorders, such as hyperthyroidism, and certain types of cancer, including thyroid cancer.DUKE
Detoxicant50247 An agent that facilitates the removal of toxins from the body, playing a crucial role in reducing oxidative stress and inflammation. Therapeutically, detoxicants are used to treat poisoning, heavy metal exposure, and liver diseases, promoting overall health and well-being by neutralizing harmful substances.DUKE
Glucosyl-transferase inhibitor23924 An agent that blocks the activity of glucosyl-transferase enzymes, preventing glycoprotein and glycolipid synthesis. It has therapeutic applications in cancer, infectious diseases, and inflammatory disorders, with key medical uses including anti-tumor, anti-viral, and anti-inflammatory treatments.DUKE
HemostaticAn agent that arrests the flow of blood within the vessels, playing a crucial biological role in wound healing and clot formation. Therapeutically, hemostatics are used to control bleeding, with key medical applications in surgery, trauma, and management of bleeding disorders, such as hemophilia.DUKE
Hepatoprotective62868 An agent that protects the liver from damage, promoting liver health and function. It plays a biological role in reducing oxidative stress and inflammation, and has therapeutic applications in managing liver diseases, such as hepatitis and cirrhosis, and key medical uses in treating drug-induced liver injury and toxicities.DUKE
HIV-reverse-transcriptase inhibitor23924 An agent that blocks the activity of reverse transcriptase, an enzyme essential for HIV replication, reducing viral load and slowing disease progression. Therapeutically, it is used to treat HIV/AIDS, often in combination with other antiretroviral medications to prevent drug resistance and manage symptoms.DUKE
JuvabionalA regulator of insect development, reproduction, and growth, juvenile hormone inhibitor, used in pest control and insecticide development, with potential applications in agriculture and entomology.DUKE
Pesticide25944 An agent that kills or repels pests, playing a biological role in controlling insect, weed, and fungal populations. Therapeutically, pesticides have limited applications, but some are used to treat ectoparasitic infestations, such as lice and scabies. Key medical uses include topical treatments for head lice and scabies, highlighting their role in managing parasitic infections.DUKE
Quinone-reductase inducerAn agent that stimulates quinone reductase enzymatic activity, enhancing cellular antioxidant defenses and protecting against carcinogens, with therapeutic applications in cancer chemoprevention and potential uses in managing oxidative stress-related diseases.DUKE
Sunscreen52217 A topical agent that blocks UV radiation, preventing skin damage and reducing the risk of skin cancer. Its therapeutic applications include protection against sunburn, photoaging, and photodermatoses. Key medical uses include prevention of melanoma, basal cell carcinoma, and squamous cell carcinoma, as well as management of photosensitive disorders.DUKE
Topoisomerase-I antagonist50276 An agent that inhibits topoisomerase-I, an enzyme involved in DNA replication, reducing cancer cell growth. Therapeutically, it's used in cancer treatment, particularly for solid tumors, as it induces DNA damage and apoptosis in cancer cells, making it a key component in chemotherapy regimens.DUKE
Xanthine oxidase inhibitor35634 An agent that blocks xanthine oxidase, an enzyme involved in uric acid production, reducing inflammation and oxidative stress. Therapeutically, it's used to treat gout, hyperuricemia, and prevent kidney stones, with key applications in managing cardiovascular disease and improving kidney function.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.