Theobromine

Modify Date: 2024-01-02 15:30:42

Theobromine Structure
Theobromine structure
 Common Name Theobromine
CAS Number 83-67-0 Molecular Weight 180.164
Density 1.6±0.1 g/cm3 Boiling Point 495.5±37.0 °C at 760 mmHg
Molecular Formula C7H8N4O2 Melting Point 345-350 °C
MSDS Chinese USA Flash Point 253.5±26.5 °C
Symbol GHS02 GHS06 GHS08
GHS02, GHS06, GHS08		 Signal Word Danger

 Use of Theobromine


Theobromine is a methylxanthine found in cacao beans which can inhibit adenosine receptor A1 (AR1) signaling.

 Names

Name theobromine
Synonym More Synonyms

 Theobromine Biological Activity

Description Theobromine is a methylxanthine found in cacao beans which can inhibit adenosine receptor A1 (AR1) signaling.
Related Catalog
Target

Human Endogenous Metabolite
In Vitro Theobromine, at concentrations above 25 μM, decreases lipid accumulation in these cells. Cell viability is not affected by Theobromine. Theobromine, at concentrations above 25 μM, suppresses protein expression of PPARγ, C/EBPα and adipogenic genes. The mRNA levels of these genes are also decreased by Theobromine[1].
In Vivo Body weights are lower in the Theobromine group than in the vehicle group. In addition, Theobromine suppresses gains in weight of epididymal and perirenal adipose tissues. The mean adipocyte area is smaller in the Theobromine group than in the vehicle group[1]. Theobromine group shows lower counts than the other groups when considering the number of bacteria per fecal weight (p=0.021 and p=0.055 compare to the reference (RF) and the cocoa (CC) groups, respectively). The Theobromine diet leads to higher pH values than those found after the RF and CC diets. Fecal concentrations of lactic acid are not significantly affected by the experimental diets (4.26±1.54 mM in RF group; 1.96±0.41 mM in CC group; 2.69±0.73 mM in Theobromine group)[2].
Kinase Assay 3T3-L1 preadipocytes are pre-incubated with MG132 (10 μM) for 30 min, followed by incubation with IBMX in the presence or absence of Theobromine (25 μM) for 8 h. The cells are lysed in denaturing cell extraction buffer (50 mM Tris-HCl, pH 7.5, containing 70 mM β-mercaptoethanol and 2% SDS) at 95°C for 10 min. The cell lysates are diluted 20 fold with dilution buffer (20 mM Tris-HCl, pH 7.5, containing 150 mM NaCl, 1 mM EDTA, 1mM EGTA, 1% TritonX-100, 2.5 mM sodium pyrophosphate and protease inhibitor cocktail) and centrifuged at 20,000 g for 30 s. The supernatant is incubated with rabbit polyclonal anti-C/EBPβ IgG, anti-FLAG IgG or control IgG at 4°C overnight, followed by incubation with 30 μL protein G-Sepharose resin at 4°C for 1 h. The resin is washed with lysis buffer three times and proteins bound to the resin are separated by SDS-PAGE and analyzed by western blotting[1].
Animal Admin Lewis rats (3 week old) are used in this study. The rats are randomly distributed into three dietary groups (n=7 per group): the reference (RF) group ingested standard diet AIN-93M, the cocoa (CC) group ingested a standard diet with 10% of natural Forastero cocoa containing 0.25% Theobromine, and the Theobromine (TB) group ingested a standard diet including 0.25% of Theobromine, i.e. the content of Theobromine presents in the CC diet[2].
References

[1]. Mitani T, et al. Theobromine suppresses adipogenesis through enhancement of CCAAT-enhancer-binding protein β degradation by adenosine receptor A1.

[2]. Martín-Peláez S, et al. Effect of cocoa's theobromine on intestinal microbiota of rats. Mol Nutr Food Res. 2017 Oct;61(10).

 Chemical & Physical Properties

Density 1.6±0.1 g/cm3
Boiling Point 495.5±37.0 °C at 760 mmHg
Melting Point 345-350 °C
Molecular Formula C7H8N4O2
Molecular Weight 180.164
Flash Point 253.5±26.5 °C
Exact Mass 180.064728
PSA 72.68000
LogP -2.08
Vapour Pressure 0.0±1.3 mmHg at 25°C
Index of Refraction 1.737
Storage condition Refrigerator
Water Solubility slightly soluble,

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
XH2275000
CHEMICAL NAME :
Theobromine
CAS REGISTRY NUMBER :
83-67-0
BEILSTEIN REFERENCE NO. :
0016464
LAST UPDATED :
199701
DATA ITEMS CITED :
40
MOLECULAR FORMULA :
C7-H8-N4-O2
MOLECULAR WEIGHT :
180.19
WISWESSER LINE NOTATION :
T56 BN DN FNVMVJ B1 F1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human
DOSE/DURATION :
26 mg/kg
TOXIC EFFECTS :
Behavioral - changes in motor activity (specific assay) Gastrointestinal - nausea or vomiting
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1265 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
837 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
552 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
530 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
300 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - cat
DOSE/DURATION :
200 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
1 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
11596 mg/kg/28D-C
TOXIC EFFECTS :
Endocrine - changes in thymus weight Related to Chronic Data - changes in testicular weight
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
4172 gm/kg/49D-C
TOXIC EFFECTS :
Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - changes in testicular weight
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
23520 mg/kg/7W-C
TOXIC EFFECTS :
Behavioral - food intake (animal) Endocrine - changes in thymus weight Related to Chronic Data - changes in testicular weight
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
39900 mg/kg/19W-C
TOXIC EFFECTS :
Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - changes in testicular weight
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
40320 mg/kg/28D-C
TOXIC EFFECTS :
Endocrine - other changes Nutritional and Gross Metabolic - weight loss or decreased weight gain Related to Chronic Data - death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
4 gm/kg/28D-C
TOXIC EFFECTS :
Cardiac - other changes
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
30400 mg/kg/43W-C
TOXIC EFFECTS :
Cardiac - other changes
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - hamster
DOSE/DURATION :
33600 mg/kg/28D-C
TOXIC EFFECTS :
Behavioral - food intake (animal) Endocrine - changes in thymus weight
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
7500 mg/kg
SEX/DURATION :
male 49 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - testes, epididymis, sperm duct
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
17640 mg/kg
SEX/DURATION :
male 49 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Fertility - male fertility index (e.g. # males impregnating females per # males exposed to fertile nonpregnant females)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
6300 mg/kg
SEX/DURATION :
female 1-21 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - live birth index (measured after birth) Reproductive - Effects on Newborn - growth statistics (e.g.%, reduced weight gain)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
500 mg/kg
SEX/DURATION :
female 13 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus) Reproductive - Specific Developmental Abnormalities - craniofacial (including nose and tongue) Reproductive - Specific Developmental Abnormalities - musculoskeletal system
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
500 mg/kg
SEX/DURATION :
female 13 day(s) after conception
TOXIC EFFECTS :
Reproductive - Specific Developmental Abnormalities - other developmental abnormalities
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
3 gm/kg
SEX/DURATION :
female 6-29 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)

MUTATION DATA

TEST SYSTEM :
Rodent - hamster
DOSE/DURATION :
300 mg/kg
REFERENCE :
EXPEAM Experientia. (Birkhaeuser Verlag, POB 133, CH-4010 Basel, Switzerland) V.1- 1945- Volume(issue)/page/year: 38,600,1982 *** REVIEWS *** IARC Cancer Review:Human Inadequate Evidence IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 51,421,1991 IARC Cancer Review:Animal No Available Data IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 51,421,1991 IARC Cancer Review:Group 3 IMEMDT IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man. (WHO Publications Centre USA, 49 Sheridan Ave., Albany, NY 12210) V.1- 1972- Volume(issue)/page/year: 51,421,1991 TOXICOLOGY REVIEW JRPMAP Journal of Reproductive Medicine. (2 Jacklynn Ct., St. Louis, MO 63132) V.3- 1969- Volume(issue)/page/year: 12,27,1974 TOXICOLOGY REVIEW FAATDF Fundamental and Applied Toxicology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1981- Volume(issue)/page/year: 13,747,1989

 Safety Information

Symbol GHS02 GHS06 GHS08
GHS02, GHS06, GHS08
Signal Word Danger
Hazard Statements H225-H301 + H311 + H331-H370
Precautionary Statements P210-P260-P280-P301 + P310-P311
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes Xn:Harmful;
Risk Phrases R22
Safety Phrases S22-S24/25
RIDADR 2811.0
WGK Germany 1
RTECS XH2275000
Hazard Class 6.1
HS Code 2933990090

 Synthetic Route

 Customs

HS Code 2933990090
Summary 2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

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 Synonyms

3,7-Dimethyl-xanthine
Diurobromine
1H-Purine-2,6-dione, 3,7-dihydro-3,7-dimethyl-
EINECS 201-494-2
Teobromin
Theostene
2,6-Dihydroxy-3,7-dimethyl-purine
Theobromine
Diuretin
Thesal
3,7-Dimethyl-3,7-dihydro-1H-purine-2,6-dione
3,7-dimethylpurine-2,6-dione
Theosalvose
Theobromin
3,7-dimethyl xanthine
Thesodate
5-26-13-00553 (Beilstein Handbook Reference)
Santheose
3,7-dihydro-3,7-dimethyl-1H-purine-2,6-dione
MFCD00022830
Top Suppliers:I want be here
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  • Product Name: Theobromine
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Related Compounds: More...
THEOBROMINE
519-41-5
Theobromine-d6
117490-40-1
Allyltheobromine
2530-99-6
Theobromine ethyl
7464-74-6
1-sodiotheobromine
1010-59-9
1-Butyltheobromine
1143-30-2
1-Ethyl theobromine
39832-36-5
1-Butyl theobromine
63906-57-0
1-Propyl theobromine
63906-63-8
Chemsrc provides Theobromine(CAS#:83-67-0) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of Theobromine are included as well.>> amp version: Theobromine

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