bilirubin

Names

[ CAS No. ]:
635-65-4

[ Name ]:
bilirubin

[Synonym ]:
(4Z,15Z)-Bilirubin IXa
21H-Biline-8,12-dipropanoic acid, 2,17-diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-
Bilirubin: 21H-Biline-8,12-dipropanoicacid,2,17-diethenyl-1,10,19,22,23,24-hexahydro-3,7,13,18-tetramethyl-1,19-dioxo-,
Biliyubin
filirubin
Cholerythrin
EINECS 211-239-7
(Z,Z)-Bilirubin
3-{2-({3-(2-Carboxyethyl)-4-methyl-5-[(Z)-(3-methyl-5-oxo-4-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene)methyl]-1H-pyrrol-2-yl}methyl)-4-methyl-5-[(Z)-(4-methyl-5-oxo-3-vinyl-1,5-dihydro-2H-pyrrol-2-ylidene)methyl]-1H-pyrrol-3-yl}propanoic acid
1,10,19,22,23,24-hexahydro-2,7,13,17-tetramethyl-1,19-dioxo-3,18-divinyl-Biline-8,12-dipropionic acid
bilirubin
1,3,6,7-Tetramethyl-4,5-dicarboxyethyl-2,8-divinyl-(b-13)-dihydrobilenone
hemetoidin
(Z,Z)-Bilirubin IXa
Bilirubin IXa
MFCD00005499

Biological Activity

[Description]:

Bilirubin is a yellow breakdown product of heme catabolism.

[Related Catalog]:

Natural Products >> Acids and Aldehydes

Research Areas >> Cardiovascular Disease

[Target]

Human Endogenous Metabolite

[In Vitro]

Unconjugated Bilirubin inhibits the cleavage of F485-rVWF73-H, D633-rVWF73-H, and GST-rVWF71-11K by ADAMTS13 in a concentration-dependent manner with a half-maximal inhibitory concentration (IC50) of ~13 μM, ~70 μM, and ~17 μM, respectively. Unconjugated Bilirubin also dose-dependently inhibits the cleavage of multimeric VWF by ADAMTS13 under denaturing conditions[1]. Bilirubin exhibits antioxidant and antimutagenic effects in vitro[2].

[References]

[1]. Lu RN, et al. Unconjugated Bilirubin inhibits proteolytic cleavage of von Willebrand factor by ADAMTS13 protease. J Thromb Haemost. 2015 Jun;13(6):1064-72.

[2]. Mölzer C, et al. Bilirubin and related tetrapyrroles inhibit food-borne mutagenesis: a mechanism for antigenotoxic action against a model epoxide. J Nat Prod. 2013 Oct 25;76(10):1958-65.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.2163

[ Boiling Point ]:
641.7°C

[ Melting Point ]:
192 °C

[ Molecular Formula ]:
C₃₃H₃₆N₄O₆

[ Molecular Weight ]:
584.662

[ Flash Point ]:
478.1±37.1 °C

[ Exact Mass ]:
584.263489

[ PSA ]:
164.38000

[ LogP ]:
3.15

[ Vapour Pressure ]:
0.0±0.3 mmHg at 25°C

[ Index of Refraction ]:
1.640

[ Storage condition ]:
−20°C

[ Stability ]:
Stable. Refrigerate.

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: DU3038000

CHEMICAL NAME :: Biline-8,12-dipropionic acid, 1,10,19,22,23,24-hexahydro-2,7,13,17-tetramethyl-1,19 -dioxo- 3,18-divinyl-

CAS REGISTRY NUMBER :: 635-65-4

BEILSTEIN REFERENCE NO. :: 0074376

LAST UPDATED :: 199701

DATA ITEMS CITED :: 8

MOLECULAR FORMULA :: C33-H36-N4-O6

MOLECULAR WEIGHT :: 584.73

WISWESSER LINE NOTATION :: T5VMYTJ D1 E1U1 CU1- ET5MYTJ C2VQ D1 BU1- ET5MYTJ C1 D2VQ BU1- ET5MVTJ C1 D1U1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >15 gm/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity)

REFERENCE :: ESKHA5 Eisei Shikenjo Hokoku. Bulletin of the Institute of Hygienic Sciences. (Kokuritsu Eisei Shikenjo Kagaku, 18-1 Bushitsu Johobu, Setagaya-ku, Tokyo 158, Japan) V.1- 1886- Volume(issue)/page/year: (103),29,1985

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: >2 gm/kg

TOXIC EFFECTS :: Gastrointestinal - other changes

REFERENCE :: ESKHA5 Eisei Shikenjo Hokoku. Bulletin of the Institute of Hygienic Sciences. (Kokuritsu Eisei Shikenjo Kagaku, 18-1 Bushitsu Johobu, Setagaya-ku, Tokyo 158, Japan) V.1- 1886- Volume(issue)/page/year: (103),29,1985 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 175 mg/kg

SEX/DURATION :: female 9-15 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants) Reproductive - Effects on Embryo or Fetus - fetal death

REFERENCE :: AJOGAH American Journal of Obstetrics and Gynecology. (C.V. Mosby Co., 11830 Westline Industrial Dr., St. Louis, MO 63146) V.1- 1920- Volume(issue)/page/year: 127,497,1977

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intraperitoneal

DOSE :: 25 mg/kg

SEX/DURATION :: female 12 day(s) after conception

TOXIC EFFECTS :: Reproductive - Effects on Embryo or Fetus - other effects to embryo

REFERENCE :: AJOGAH American Journal of Obstetrics and Gynecology. (C.V. Mosby Co., 11830 Westline Industrial Dr., St. Louis, MO 63146) V.1- 1920- Volume(issue)/page/year: 127,497,1977 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 81726 No. of Facilities: 114 (estimated) No. of Industries: 1 No. of Occupations: 2 No. of Employees: 1390 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 81726 No. of Facilities: 1176 (estimated) No. of Industries: 3 No. of Occupations: 7 No. of Employees: 12638 (estimated) No. of Female Employees: 9389 (estimated)

Safety Information

[ Personal Protective Equipment ]:
Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
R62

[ Safety Phrases ]:
22-24/25-36-26

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
2

[ RTECS ]:
DU3038000

[ HS Code ]:
29339990

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 29339990

Articles

Mitochondrial targeting of bilirubin regulatory enzymes: An adaptive response to oxidative stress.

Toxicol. Appl. Pharmacol. 282(1) , 77-89, (2015)

The intracellular level of bilirubin (BR), an endogenous antioxidant that is cytotoxic at high concentrations, is tightly controlled within the optimal therapeutic range. We have recently described a ...

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Org. Biomol. Chem. 13(10) , 3040-7, (2015)

Inflammatory signaling pathways orchestrate the cellular response to infection and injury. These pathways are known to be modulated by compounds that alkylate cysteinyl thiols. One class of phytochemi...