Articles:
coumarin, 3,3'-methylenebis(4-hydroxy-
Notes:
Isol. from Melilotus alba (white melilot)
Dicoumarol (INN) or dicumarol (USAN) is an anticoagulant that functions as a Vitamin K antagonist (similar to warfarin). It is also used in biochemical experiments as an inhibitor of reductases.; Dicumarol is an coumarin-like compound found in sweet clover. It is used as an oral anticoagulant and acts by inhibiting the hepatic synthesis of vitamin K-dependent coagulation factors (prothrombin and factors VII, IX, and X). It is also used in biochemical experiments as an inhibitor of reductases.; It is a derivative of coumarin.; Mechanism of action : it is a competitive inhibitor of Vitamin K preventing the formation of prothrombin , Administration of Vitamin K is the antidote for dicumarol toxicity; also that Dicumarol is a chemical subsrance of plant origin given only orally and acts within two days
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| CAS Number: | 66-76-2 |  3D/inchi
|
| ECHA EINECS - REACH Pre-Reg: | 200-632-9 | |
| FDA UNII: | 7QID3E7BG7 | |
| Nikkaji Web: | J4.845C | |
| Beilstein Number: | 0335444 | |
| MDL: | MFCD00006857 | |
| XlogP3-AA: | 2.60 (est) | |
| Molecular Weight: | 336.29984000 | |
| Formula: | C19 H12 O6 | |
| NMR Predictor: | Predict (works with chrome or firefox) | |
Category: natural substances and extractives
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
| Google Scholar: | Search |
| Google Books: | Search |
| Google Scholar: with word "volatile" | Search |
| Google Scholar: with word "flavor" | Search |
| Google Scholar: with word "odor" | Search |
| Google Patents: | Search |
| US Patents: | Search |
| EU Patents: | Search |
| Pubchem Patents: | Search |
| PubMed: | Search |
| NCBI: | Search |
Physical Properties:
| Assay: | 95.00 to 100.00 % |
| Food Chemicals Codex Listed: | No |
| Soluble in: | |
| water, 127.8 mg/L @ 25 °C (est) | |
Organoleptic Properties:
| Odor and/or flavor descriptions from others (if found). | |
Cosmetic Information:
| None found |
Suppliers:
| Alfa Biotechnology |
| For experimental / research use only. |
| Dicumarol 98% |
| BOC Sciences |
| For experimental / research use only. |
| Dicoumarol >98%
Odor: characteristic Use: A cell-permeable quinone reductase inhibitor with anticoagulant properties. Potentiates apoptosis by simultaneously blocking SAPK/JNK and NF-aB pathways without affecting phosphorylation of p38 or activation of AKT. |
| Santa Cruz Biotechnology |
| For experimental / research use only. |
| Dicumarol ≥98% |
| Sigma-Aldrich: Sigma |
| For experimental / research use only. |
| 3,3'-Methylene-bis(4-hydroxycoumarin) |
Safety Information:
| Preferred SDS: View | |
| 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 | |
| Pictogram | |
| Hazard statement(s) | |
| None found. | |
| Precautionary statement(s) | |
| None found. | |
| Oral/Parenteral Toxicity: | |
|
intravenous-dog LDLo 40 mg/kg "Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. 57, 1973. intravenous-guinea pig LD50 59 mg/kg GASTROINTESTINAL: ULCERATION OR BLEEDING FROM LARGE INTESTINE SENSE ORGANS AND SPECIAL SENSES: ULCERATED NASAL SEPTUM: OLFACTION Proceedings of the Society for Experimental Biology and Medicine. Vol. 50, Pg. 228, 1942. intraperitoneal-mouse LD50 91 mg/kg CARDIAC: OTHER CHANGES VASCULAR: PULSE PRESSURE INCREASE Dissertationes Pharmaceuticae. Vol. 17, Pg. 163, 1965. intravenous-mouse LD50 42 mg/kg Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 222, Pg. 107, 1954. oral-mouse LD50 233 mg/kg SENSE ORGANS AND SPECIAL SENSES: ULCERATED NASAL SEPTUM: OLFACTION GASTROINTESTINAL: ULCERATION OR BLEEDING FROM LARGE INTESTINE Proceedings of the Society for Experimental Biology and Medicine. Vol. 50, Pg. 228, 1942. intravenous-rabbit LD50 22 mg/kg Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 222, Pg. 107, 1954. oral-rabbit LD50 75 mg/kg Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 222, Pg. 107, 1954. intravenous-rat LD50 52 mg/kg GASTROINTESTINAL: ULCERATION OR BLEEDING FROM LARGE INTESTINE SENSE ORGANS AND SPECIAL SENSES: ULCERATED NASAL SEPTUM: OLFACTION Proceedings of the Society for Experimental Biology and Medicine. Vol. 50, Pg. 228, 1942. oral-rat LD50 250 mg/kg Schweizerische Medizinische Wochenschrift. Vol. 83, Pg. 471, 1953. | |
| Dermal Toxicity: | |
|
subcutaneous-mouse LD50 50 mg/kg "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 8(1), Pg. 360, 1982. | |
| Inhalation Toxicity: | |
| Not determined | |
Safety in Use Information:
| Category: | natural substances and extractives | ||
| Recommendation for dicumarol usage levels up to: | |||
| not for fragrance use. | |||
| Recommendation for dicumarol flavor usage levels up to: | |||
| not for flavor use. | |||
Safety References:
| EPI System: | View |
| Chemical Carcinogenesis Research Information System: | Search |
| AIDS Citations: | Search |
| Cancer Citations: | Search |
| Toxicology Citations: | Search |
| EPA ACToR: | Toxicology Data |
| EPA Substance Registry Services (SRS): | Registry |
| Laboratory Chemical Safety Summary : | 54676038 |
| National Institute of Allergy and Infectious Diseases: | Data |
| WGK Germany: | 3 |
| 4-hydroxy-3-[(4-hydroxy-2-oxochromen-3-yl)methyl]chromen-2-one | |
| Chemidplus: | 0000066762 |
| RTECS: | GN7875000 for cas# 66-76-2 |
References:
| 4-hydroxy-3-[(4-hydroxy-2-oxochromen-3-yl)methyl]chromen-2-one | |
| NIST Chemistry WebBook: | Search Inchi |
| Pubchem (cid): | 54676038 |
| Pubchem (cas): | 66-76-2 |
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 |
| CHEBI: | View |
| CHEMBL: | View |
| KEGG (GenomeNet): | C00796 |
| HMDB (The Human Metabolome Database): | HMDB14411 |
| FooDB: | FDB012523 |
| Export Tariff Code: | 2932.29.4500 |
| VCF-Online: | VCF Volatile Compounds in Food |
| ChemSpider: | View |
| Wikipedia: | View |
Potential Blenders and core components note
| None Found | ||
Potential Uses:
| None Found |
Occurrence (nature, food, other): note
| melilotus alba Search Trop Picture |
Synonyms:
| antitrombosin | |
| 2H-1- | benzopyran-2-one, 3,3'-methylenebis(4-hydroxy- |
| coumarin, 3,3'-methylenebis(4-hydroxy- | |
| 4- | hydroxy-3-[(4-hydroxy-2-oxochromen-3-yl)methyl]chromen-2-one |
| bis(4- | hydroxycoumarin-3-yl)methane |
| kumoran | |
| 3,3'- | methylenebis(4-hydroxy-2H-1-benzopyran-2-one) |
| temparin | |
| trombosan |