theobromine

3,7-dimethylpurine-2,6-dione

CAS: 83-67-0 C7 H8 N4 O2 MW: 180.16716000 bitter

Identification

Nametheobromine
IUPAC3,7-dimethylpurine-2,6-dione
CAS Number83-67-0
EINECS201-494-2
FDA UNIIOBD445WZ5P
Molecular FormulaC7 H8 N4 O2
Molecular Weight180.16716000
MDL NumberMFCD00022830
Nikkaji NumberJ3.874A
Beilstein0016464
XlogP3-0.80 (est)

Regulatory

FDA/DG SANTE Petitions, Reviews, NoticesGRN 340
DG SANTE Food Flavourings16.032 theobromine
FEMA Number3591
FDANo longer provide for the use of these seven synthetic flavoring substances
FDA Mainterm (SATF)83-67-0 ; THEOBROMINE

Physical Properties

Appearance white powder (est)
Assay 98.00 to 100.00
Food Chemicals Codex Listed No
Melting Point 345.00 to 350.00 °C. @ 760.00 mm Hg
Flash Point 32.00 °F. TCC ( 0.00 °C. ) (est)
logP (o/w) -0.780
Shelf Life 24.00 month(s) or longer if stored properly.
Storage store in cool, dry place in tightly sealed containers, protected from heat and light.
Soluble in alcohol
Insoluble in water

Cosmetic Information

CosIngcosmetic data
Cosmetic Usesfragrance

Organoleptic Properties

Taste Description bitter

Safety Information

Preferred SDSView
European informationMost important hazard(s):
Oral/Parenteral Toxicityoral-rat LD50 1265 mg/kg
Dermal Toxicitysubcutaneous-rabbit LDLo 1000 mg/kg
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categoryflavoring agents
Recommendation for theobromine usage levels up tonot for fragrance use.
Maximised Survey-derived Daily Intakes (MSDI-EU)30.00 (μg/capita/day)
Structure ClassIII
baked goods-
beverages(nonalcoholic)-
beverages(alcoholic)-
breakfast cereal-
cheese-
chewing gum-
condiments / relishes-
confectionery froastings-
egg products-
fats / oils-
fish products-
frozen dairy-
fruit ices-
gelatins / puddings-
granulated sugar-
gravies-
hard candy-
imitation dairy-
instant coffee / tea-
jams / jellies-
meat products-
milk products-
nut products-
other grains-
poultry-
processed fruits-
processed vegetables-
reconstituted vegetables-
seasonings / flavors-
snack foods-
soft candy-
soups-
sugar substitutes-
sweet sauces-
Dairy products, excluding products of category 02.0 (01.0)20.00000
Fats and oils, and fat emulsions (type water-in-oil) (02.0)-
Edible ices, including sherbet and sorbet (03.0)-
Processed fruit (04.1)-
Processed vegetables (incl. mushrooms & fungi, roots & tubers, pulses and legumes), and nuts & seeds (04.2)-
Confectionery (05.0)-
Chewing gum (05.3)-
Cereals and cereal products, incl. flours & starches from roots & tubers, pulses & legumes, excluding bakery (06.0)-
Bakery wares (07.0)-
Meat and meat products, including poultry and game (08.0)-
Fish and fish products, including molluscs, crustaceans and echinoderms (MCE) (09.0)-
Eggs and egg products (10.0)-
Sweeteners, including honey (11.0)-
Salts, spices, soups, sauces, salads, protein products, etc. (12.0)-
Foodstuffs intended for particular nutritional uses (13.0)-
Non-alcoholic ("soft") beverages, excl. dairy products (14.1)75.00000
Alcoholic beverages, incl. alcohol-free and low-alcoholic counterparts (14.2)-
Ready-to-eat savouries (15.0)-
Composite foods (e.g. casseroles, meat pies, mincemeat) - foods that could not be placed in categories 01.0 - 15.0 (16.0)-

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Potential Uses

None Found

Natural Occurrence

cacao bean cacao petiole cacao testa cocoa bean cocoa petiole coffee bean coffee leaf guarana kola nut lemon pomelo tea anther tea flower tea leaf tea pericarp tea seed tea seed coat tea stem

Synonyms

3,7- dihydro-3,7-dimethyl-1H-purine-2,6-dione 2,6- dihydroxy-3,7-dimethyl purine 2,6- dihydroxy-3,7-dimethyl-purine 2,6- dihydroxy-3,7-dimethylpurine 3,7- dimethyl xanthine 3,7- dimethyl-1,3,7-trihydropurine-2,6-dione 3,7- dimethyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione 3,7- dimethyl-3,7-dihydro-1H-purine-2,6-dione 3,7- dimethyl-xanthine 3,7- dimethylpurine-2,6-dione 3,7- dimethylxanthine diuretin diurobromine 1H- purine-2, 3,7-dihydro-3,7-dimethyl- 1H- purine-2,6-dione, 3,7-dihydro-3,7-dimethyl- 1H- purine-2,6-dione,3,7-dihydro-3,7- dimethyl- teobromin theobromin theobromine natural theosalvose theostene thesodate xanthine, 3,7-dimethyl- US Patents: 4,006,261 - Flavoring with mixtures of theobromine and cyclic dipeptides PubMed: Theobromine enhances absorption of cacao polyphenol in rats. PubMed: Differing chemical compositions of three teas may explain their different effects on acute blood pressure in spontaneously hypertensive rats. PubMed: Quantitative analysis of major constituents in green tea with different plucking periods and their antioxidant activity. PubMed: Alkaloids and athlete immune function: caffeine, theophylline, gingerol, ephedrine, and their congeners. PubMed: Identification and determination of synthetic pharmaceuticals as adulterants in eight common herbal weight loss supplements. PubMed: Interactions among chemical components of Cocoa tea (Camellia ptilophylla Chang), a naturally low caffeine-containing tea species. PubMed: Cocoa phytochemicals: recent advances in molecular mechanisms on health. PubMed: Diet of patients after pouch surgery may affect pouch inflammation. PubMed: Health benefits of methylxanthines in cacao and chocolate. PubMed: Simultaneous determination of caffeine, theophylline and theobromine in food samples by a kinetic spectrophotometric method. PubMed: Simultaneous quantification of caffeine and its three primary metabolites in rat plasma by liquid chromatography-tandem mass spectrometry. PubMed: Fuzhuanins A and B: the B-ring fission lactones of flavan-3-ols from Fuzhuan brick-tea. PubMed: [About flavouring substances and flavouring preparations regulation in the field of manufacturing of flavourings and foodstuffs]. PubMed: Concentration of biologically active compounds extracted from Ilex paraguariensis St. Hil. by nanofiltration. PubMed: Cocoa and human health. PubMed: Guarana powder polysaccharides: characterisation and evaluation of the antioxidant activity of a pectic fraction. PubMed: Development and validation of a rapid ultra high pressure liquid chromatographic method for the determination of methylxanthines in herbal infusions. PubMed: Involvement of a novel intronic microRNA in cross regulation of N-methyltransferase genes involved in caffeine biosynthesis in Coffea canephora. PubMed: Diversity of cacao trees in Waslala, Nicaragua: associations between genotype spectra, product quality and yield potential. PubMed: Dietary nutrients associated with short and long sleep duration. Data from a nationally representative sample. PubMed: The protective effects of guaraná extract (Paullinia cupana) on fibroblast NIH-3T3 cells exposed to sodium nitroprusside. PubMed: Profiles of phenolic compounds and purine alkaloids during the development of seeds of Theobroma cacao cv. Trinitario. PubMed: Modification of ginseng flavors by bitter compounds found in chocolate and coffee. PubMed: Influence of sugar type on the bioavailability of cocoa flavanols. PubMed: Development of a chromatographic low pressure flow injection system: application to the analysis of methylxanthines in coffee. PubMed: A general strategy for performing temperature-programming in high performance liquid chromatography--further improvements in the accuracy of retention time predictions of segmented temperature gradients. PubMed: Alkaloids in the human food chain--natural occurrence and possible adverse effects. PubMed: Comparison of the chemical constituents of aged pu-erh tea, ripened pu-erh tea, and other teas using HPLC-DAD-ESI-MSn. PubMed: Erythema multiforme-like eruption from a slimming drug preparation cutaneous adverse drug reaction. PubMed: Flavanols and methylxanthines in commercially available dark chocolate: a study of the correlation with nonfat cocoa solids. PubMed: Rapid methods to determine procyanidins, anthocyanins, theobromine and caffeine in rat tissues by liquid chromatography-tandem mass spectrometry. PubMed: Blood levels of vitamin D in teens and young adults with myopia. PubMed: Caffeine, pentoxifylline and theophylline form stacking complexes with IQ-type heterocyclic aromatic amines. PubMed: Theobromine and the pharmacology of cocoa. PubMed: Natural compounds in the human diet and their ability to bind mutagens prevents DNA-mutagen intercalation. PubMed: Energy drinks: a review of use and safety for athletes. PubMed: Phenolic acids and methylxanthines composition and antioxidant properties of mate (Ilex paraguariensis) residue. PubMed: Rapid determination of methylxanthines in real samples by high-performance liquid chromatography using the new FastGradient narrow-bore monolithic column. PubMed: Methylxanthines and phenolics content extracted during the consumption of mate (Ilex paraguariensis St. Hil) beverages. PubMed: Natural cocoa as diet-mediated antimalarial prophylaxis. PubMed: Identification of a major polyphenol and polyphenolic composition in leaves of Camellia irrawadiensis. PubMed: Rapid determination of phenolic compounds and alkaloids of carob flour by improved liquid chromatography tandem mass spectrometry. PubMed: Cilostazol: new drug. Intermittent claudication: too little efficacy, too many risks. PubMed: Antihypertensive effect of a polyphenol-rich cocoa powder industrially processed to preserve the original flavonoids of the cocoa beans. PubMed: Validity and reproducibility of a self-administered semi-quantitative food-frequency questionnaire for estimating usual daily fat, fibre, alcohol, caffeine and theobromine intakes among Belgian post-menopausal women. PubMed: Pharmacologic therapy for intermittent claudication. PubMed: Safety assessment of kola nut extract as a food ingredient. PubMed: Pentoxifylline: a drug with wide spectrum applications in dermatology. PubMed: Anti-TNF treatment reduces rat skeletal muscle wasting in monocrotaline-induced cardiac cachexia. PubMed: Quantitation of methylxanthinic alkaloids and phenolic compounds in mate (Ilex paraguariensis) and their effects on blood vessel formation in chick embryos. PubMed: Protection of human HepG2 cells against oxidative stress by cocoa phenolic extract. PubMed: Effects of chronic administration of caffeine and stress on feeding behavior of rats. PubMed: Simultaneous HPLC determination of caffeine, theobromine, and theophylline in food, drinks, and herbal products. PubMed: Determination of caffeine and associated compounds in food, beverages, natural products, pharmaceuticals, and cosmetics by micellar electrokinetic capillary chromatography. PubMed: Short-term toxicity of aristolochic acid, aristolochic acid-I and aristolochic acid-II in rats. PubMed: Predictive relationship between polyphenol and nonfat cocoa solids content of chocolate. PubMed: Chemical and archaeological evidence for the earliest cacao beverages. PubMed: Lipopolysaccharide and trovafloxacin coexposure in mice causes idiosyncrasy-like liver injury dependent on tumor necrosis factor-alpha. PubMed: Influence of peptone source on sporulation of Clostridium perfringens type A. PubMed: Selective liquid CO2 extraction of purine alkaloids in different Ilex paraguariensis progenies grown under environmental influences. PubMed: Simultaneous analysis of catechins, gallic acid, strictinin, and purine alkaloids in green tea by using catechol as an internal standard. PubMed: Microbial and dietary factors associated with the 8-prenylnaringenin producer phenotype: a dietary intervention trial with fifty healthy post-menopausal Caucasian women. PubMed: Urinary excretion of dietary contaminants in horses. PubMed: Development of a biosensor for caffeine. PubMed: Infection and anorexia. PubMed: Overview of antibacterial, antitoxin, antiviral, and antifungal activities of tea flavonoids and teas. PubMed: Molecular definition of the taste of roasted cocoa nibs (Theobroma cacao) by means of quantitative studies and sensory experiments. PubMed: Antimicrobial activities of tea catechins and theaflavins and tea extracts against Bacillus cereus. PubMed: Pentoxifylline in ALS: a double-blind, randomized, multicenter, placebo-controlled trial. PubMed: The pivotal role of cytokines in muscle wasting during cancer. PubMed: Sensory-guided decomposition of roasted cocoa nibs (Theobroma cacao) and structure determination of taste-active polyphenols. PubMed: Solid-phase ultraviolet sensing system for determination of methylxanthines. PubMed: Evaluation of cocoa- and coffee-derived methylxanthines as toxicants for the control of pest coyotes. PubMed: Reinforcing effects of caffeine and theobromine as found in chocolate. PubMed: Classification of Ilex species based on metabolomic fingerprinting using nuclear magnetic resonance and multivariate data analysis. PubMed: Uric acid or 1-methyl uric acid in the urinary bladder increases serum glucose, insulin, true triglyceride, and total cholesterol levels in Wistar rats. PubMed: Plant biochemistry: a naturally decaffeinated arabica coffee. PubMed: Dietary sources of nutrients among US adults, 1994 to 1996. PubMed: Determination of caffeine, theobromine, and theophylline in standard reference material 2384, baking chocolate, using reversed-phase liquid chromatography. PubMed: HPLC-MSn analysis of phenolic compounds and purine alkaloids in green and black tea. PubMed: Influence of agronomic variables on the composition of mate tea leaves (Ilex paraguariensis) extracts obtained from CO2 extraction at 30 degrees C and 175 bar. PubMed: Lisofylline, a novel anti-inflammatory agent, enhances glucose-stimulated insulin secretion in vivo and in vitro: studies in prediabetic and normal rats. PubMed: Metabolite profiling using (1)H NMR spectroscopy for quality assessment of green tea, Camellia sinensis (L.). PubMed: Effects of coffee components on the response of GABA(A) receptors expressed in Xenopus oocytes. PubMed: Chocolate feeding of pregnant mice influences length of limbs of their progeny. PubMed: Producing decaffeinated coffee plants. PubMed: [Simultaneous determination of various food additives by high performance liquid chromatography]. PubMed: The role of Kupffer cells and TNF-alpha in monocrotaline and bacterial lipopolysaccharide-induced liver injury. PubMed: Value assignment of nutrient concentrations in standard reference material 2384 baking chocolate. PubMed: Inhibition of alkaline phosphatase activity of boar semen by pentoxifylline, caffeine, and theophylline. PubMed: Characterization of T lymphocyte subtypes in endotoxin-induced uveitis and effect of pentoxifylline treatment. PubMed: Caffeine potentiates the discriminative-stimulus effects of nicotine in rats. PubMed: Extraction of methylxanthines from guaraná seeds, maté leaves, and cocoa beans using supercritical carbon dioxide and ethanol. PubMed: Cacao usage by the earliest Maya civilization. PubMed: Study of catechin and xanthine tea profiles as geographical tracers. PubMed: Short-term toxicity of grass carp bile powder, 5alpha-cyprinol and 5alpha-cyprinol sulfate in rats. PubMed: Simultaneous determination of artificial sweeteners, preservatives, caffeine, theobromine and theophylline in food and pharmaceutical preparations by ion chromatography. PubMed: Food of the gods as mortals' medicine: the uses of choclate and cacao products. PubMed: Developmental variation of sugars, carboxylic acids, purine alkaloids, fatty acids, and endoproteinase activity during maturation of Theobroma cacao L. seeds. PubMed: Changes of gastric lipase activity after ethanol and indomethacin administration: influence of pretreatment with allopurinol, pentoxifylline and L-DOPA. PubMed: Improved high-performance liquid chromatography method to determine theobromine and caffeine in cocoa and cocoa products. PubMed: Integrating anti-tumor necrosis factor therapy in inflammatory bowel disease: current and future perspectives. PubMed: Weight loss and delayed gastric emptying following a South American herbal preparation in overweight patients. PubMed: Caffeine-induced cardiac arrhythmia: an unrecognised danger of healthfood products. PubMed: Medical management of peripheral arterial disease. PubMed: Uncertainty factors for chemical risk assessment. human variability in the pharmacokinetics of CYP1A2 probe substrates. PubMed: Uncertainty factors for chemical risk assessment: interspecies differences in the in vivo pharmacokinetics and metabolism of human CYP1A2 substrates. PubMed: Seizure activity and unresponsiveness after hydroxycut ingestion. PubMed: Cytosolic xanthine oxidoreductase mediated bioactivation of ethanol to acetaldehyde and free radicals in rat breast tissue. Its potential role in alcohol-promoted mammary cancer. PubMed: Bacterial lipopolysaccharide enhances aflatoxin B1 hepatotoxicity in rats by a mechanism that depends on tumor necrosis factor alpha. PubMed: Inhibition of adenosine uptake and augmentation of ischemia-induced increase of interstitial adenosine by cilostazol, an agent to treat intermittent claudication. PubMed: Pharmacokinetics of pentoxifylline in dogs after oral and intravenous administration. PubMed: Caffeine and theobromine levels in selected Nigerian beverages. PubMed: Dose independent pharmacokinetics of caffeine after intravenous administration under a chronic food-limited regimen. PubMed: Caffeine and theobromine levels in chocolate couverture and coating products. PubMed: Application of near-infrared reflectance spectroscopy to the simultaneous prediction of alkaloids and phenolic substances in green tea leaves. PubMed: Extraction of purine alkaloids from maté (Ilex paraguariensis) using supercritical CO(2). PubMed: Rapid analysis of methylated xanthines in teas by an improved high-performance liquid chromatographic method using a polyvinylpolypyrroridone pre-column. PubMed: Striking regression of subcutaneous fibrosis induced by high doses of gamma rays using a combination of pentoxifylline and alpha-tocopherol: an experimental study. PubMed: Nutritive value of hot water- or cocoa-pod ash solution-treated cocoa bean cake for broiler chicks. PubMed: Inhibition of tumor necrosis factor alpha alters resistance to Mycobacterium avium complex infection in mice. PubMed: Nitric oxide deficiency, leukocyte activation, and resultant ischemia are crucial to the pathogenesis of diabetic retinopathy/neuropathy--preventive potential of antioxidants, essential fatty acids, chromium, ginkgolides, and pentoxifylline. PubMed: Liquid chromatographic determination of methylxanthines and catechins in herbal preparations containing guaraná. PubMed: Determination of caffeine and its metabolites by micellar electrokinetic capillary electrophoresis. PubMed: Recent advances in caffeine and theobromine toxicities: a review. PubMed: Oxidation of caffeine and related methylxanthines in ascorbate and polyphenol-driven Fenton-type oxidations. PubMed: Protein profiles and organoleptic properties of bread from wheat flour and full-fat or defatted fermented cocoa bean powder. PubMed: Oral and IP caffeine pharmacokinetics under a chronic food-limitation condition. PubMed: Analysis of the potential carcinogenicity of coffee and its related compounds in a medium-term liver bioassay of rats. PubMed: Green tea composition, consumption, and polyphenol chemistry. PubMed: Breast cancer and methylxanthine consumption. PubMed: Urinary excretion of theobromine in horses given contaminated pelleted food. PubMed: The effect of methylxanthines on milk volume and composition, and growth of rat pups. PubMed: The excretion of theobromine in Thoroughbred racehorses after feeding compounded cubes containing cocoa husk--establishment of a threshold value in horse urine. PubMed: Effect of methylxanthines on lactational performance of rats. PubMed: Use of flavor-amplified foods to improve nutritional status in elderly patients. PubMed: Methylxanthines: toxicity to humans. 3. Theobromine, paraxanthine and the combined effects of methylxanthines. PubMed: Methylxanthines: toxicity to humans. 1. Theophylline. PubMed: Variability in caffeine consumption from coffee and tea: possible significance for epidemiological studies. PubMed: The effect of nutritional factors on sex hormone levels in male twins. PubMed: Genotoxicity and carcinogenicity assessments of caffeine and theobromine. PubMed: Effect of pentoxifylline on Wrb antigen. PubMed: Evaluation of the genotoxicity of theobromine and caffeine. PubMed: Evaluation of the perinatal, postnatal and teratogenic effects of cocoa powder and theobromine in Sprague-Dawley/CD rats. PubMed: Evaluation of the teratogenic potential of cocoa powder and theobromine in New Zealand White rabbits. PubMed: Modulation of the behavioral effects of chlordiazepoxide by methylxanthines and analogs of adenosine in squirrel monkeys. PubMed: The fate of chronically consumed caffeine in the monkey (Macaca fascicularis). PubMed: Pentoxifylline: a new agent for intermittent claudication. PubMed: Antagonism of the behavioral effects of L-phenylisopropyladenosine (L-PIA) by caffeine and its metabolites. PubMed: High-performance liquid chromatographic determination of theobromine, theophylline and caffeine in food products. PubMed: Comparative toxicities of dietary caffeine and theobromine in the rat. PubMed: Tea: the plant and its manufacture; chemistry and consumption of the beverage. PubMed: Analytical methods for quantitation of methylxanthines. PubMed: Methylxanthine composition and consumption patterns of cocoa and chocolate products. PubMed: Central nervous system pharmacology of the dietary methylxanthines. PubMed: Theobromine metabolism. PubMed: [Effect of the harvest season on the composition of raw and fermented cotyledons of 2 varieties of cacao and shell fractions]. PubMed: Effects of caffeine, theophylline and theobromine on scheduled controlled responding in rats. PubMed: Genotoxicity of cocoa examined by microbial and mammalian systems. PubMed: [Effect of methylxanthines on urinary prostaglandin E excretion of rats acutely loaded with salt and water (author's transl)]. PubMed: The biochemistry and technology of tea manufacture. PubMed: Metabolic pathway of theobromine in the rat and identification of two new metabolites in human urine. PubMed: Effects on plasma and brain tryptophan in the rat of drugs and hormones that influence the concentration of unesterified fatty acid in the plasma. PubMed: Effect on hamster caries by purine derivatives vanillin and some tannin-containing materials. Caries in relation to food consumption and animal growth. PubMed: [Determination of Theobromine and its metabolites in urine]. PubMed: VITAMIN E CONTENT OF VEGETABLE OILS AND FATS.