dicumarol, 66-76-2

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CODE123637 CODE123637
Product(s):
66-76-2 Dicoumarol >98%
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.

Name:	4-hydroxy-3-[(4-hydroxy-2-oxochromen-3-yl)methyl]chromen-2-one
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, Edge 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)

sds

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

Articles:

PubMed:Role of NAD(P)H:quinone oxidoreductase 1 on tumor necrosis factor-alpha-induced migration of human vascular smooth muscle cells.

PubMed:Mechanism to study 1:1 stoichiometry of NADPH and alkoxyphenoxazones metabolism spectrophotometrically in subcellular biological preparations.

PubMed:Synergistic cytotoxicity of Delta(9)-tetrahydrocannabinol and butylated hydroxyanisole.

PubMed:Purification and characterization of an enzyme from Mycobacterium sp. Pyr-1, with nitroreductase activity and an N-terminal sequence similar to lipoamide dehydrogenase.

PubMed:A novel NADPH:diamide oxidoreductase activity in arabidopsis thaliana P1 zeta-crystallin.

PubMed:Modulation of halobenzene-induced hepatotoxicity by DT-diaphorase modulators, butylated hydroxyanisole and dicoumarol: evidence for possible involvement of quinone metabolites in the toxicity of halobenzenes.

PubMed:Isolation of a novel NAD(P)H-quinone oxidoreductase from the cyanobacterium Synechocystis PCC6803.

PubMed:Properties of the respiratory NAD(P)H dehydrogenase isolated from the cyanobacterium Synechocystis PCC6803.

PubMed:Molecular characterization of monodehydroascorbate radical reductase from cucumber highly expressed in Escherichia coli.

PubMed:Dicoumarol (moldy sweet clover) toxicosis in a group of Holstein calves.

PubMed:Reduction and mutagenic activation of nitroaromatic compounds by a Mycobacterium sp.

PubMed:Evaluation of vitamin K3 feed additive for prevention of sweet clover disease.

PubMed:Liquid chromatographic determination of coumarin anticoagulants in tablets: collaborative study.

PubMed:Enhancement of dicoumarol bioavailability by concomitant food intake.

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

dicumarol coumarin, 3,3'-methylenebis(4-hydroxy-

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dicumarol
coumarin, 3,3'-methylenebis(4-hydroxy-