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119-84-6

119-84-6 structure
119-84-6 structure
Name 3,4-dihydrocoumarin
Synonyms Dihydrocoumarin
MFCD00006881
2-Chromanone
EINECS 204-354-9
2H-1-Benzopyran-2-one, 3,4-dihydro-
3,4-Dihydro-1-benzopyran-2-one,Benzodihydropyrone,Hydrocou
3,4-dihydrochromen-2-one
3,4-Dihydrocoumarin
Hydrocoumarin
chroman-2-one
Description Dihydrocoumarin is a compound found in Melilotus officinalis. Dihydrocoumarin is a yeast Sir2p inhibitor. Dihydrocoumarin also inhibits human SIRT1 and SIRT2 with IC50s of 208 μM and 295 μM, respectively[1].
Related Catalog
Target

hSIRT1:208 μM (IC50)

hSIRT2:295 μM (IC50)

In Vitro Dihydrocoumarin induces a concentration-dependent inhibition of SIRT1 (IC50 of 208 μM) in an in vitro enzymatic assay. A decrease in SIRT1 deacetylase activity is observed even at micromolar doses (85±5.8 and 73±13.7% activity at 1.6 μM and 8 μM, respectively). The microtubule SIRT2 deacetylase is also inhibited with a similar dose dependency (IC50 of 295 μM)[1]. Dihydrocoumarin (1-5 mM) increases cytotoxicity in the TK6 cell line in a dose-dependent manner following a 24-h exposure. Dihydrocoumarin (1-5 mM) increases apoptosis in a dose-dependent manner in the TK6 cell line at the 6-h time point. A 5-mM dose of Dihydrocoumarin increases apoptosis at the 6-h time point in the TK6 cell line[1]. Dihydrocoumarin (1-5 mM) increases p53 lysine 373 and 382 acetylation in a dose-dependent manner in the TK6 cell line following a 24-h exposure period[1].
References

[1]. Olaharski AJ, et al. The flavoring agent Dihydrocoumarin reverses epigenetic silencing and inhibits sirtuindeacetylases. PLoS Genet. 2005 Dec;1(6):e77.
Density 1.2±0.1 g/cm3
Boiling Point 272.0±15.0 °C at 760 mmHg
Melting Point 24-25 °C(lit.)
Molecular Formula C9H8O2
Molecular Weight 148.159
Flash Point 108.4±17.8 °C
Exact Mass 148.052429
PSA 26.30000
LogP 1.80
Vapour Pressure 0.0±0.6 mmHg at 25°C
Index of Refraction 1.562
Water Solubility insoluble

CHEMICAL IDENTIFICATION

RTECS NUMBER :
MW5775000
CHEMICAL NAME :
Hydrocoumarin
CAS REGISTRY NUMBER :
119-84-6
BEILSTEIN REFERENCE NO. :
0004584
LAST UPDATED :
199710
DATA ITEMS CITED :
18
MOLECULAR FORMULA :
C9-H8-O2
MOLECULAR WEIGHT :
148.17
WISWESSER LINE NOTATION :
T66 BOVT&J

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
Standard Draize test
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent - rabbit
REFERENCE :
FCTXAV Food and Cosmetics Toxicology. (London, UK) V.1-19, 1963-81. For publisher information, see FCTOD7. Volume(issue)/page/year: 12,521,1974
TYPE OF TEST :
Standard Draize test
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent - guinea pig
REFERENCE :
JSCCA5 Journal of the Society of Cosmetic Chemists. (Soc. of Cosmetic Chemists, 1995 Broadway, Suite 1701, New York, NY 10023) V.1- 1947- Volume(issue)/page/year: 28,357,1977 ** ACUTE TOXICITY DATA **
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1460 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity)
REFERENCE :
FCTXAV Food and Cosmetics Toxicology. (London, UK) V.1-19, 1963-81. For publisher information, see FCTOD7. Volume(issue)/page/year: 2,327,1964
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
200 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NTIS** National Technical Information Service. (Springfield, VA 22161) Formerly U.S. Clearinghouse for Scientific & Technical Information. Volume(issue)/page/year: AD277-689
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Administration onto the skin
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
>5 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
FCTXAV Food and Cosmetics Toxicology. (London, UK) V.1-19, 1963-81. For publisher information, see FCTOD7. Volume(issue)/page/year: 12,521,1974
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
1760 mg/kg
TOXIC EFFECTS :
Behavioral - somnolence (general depressed activity)
REFERENCE :
FCTXAV Food and Cosmetics Toxicology. (London, UK) V.1-19, 1963-81. For publisher information, see FCTOD7. Volume(issue)/page/year: 2,327,1964 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
18 gm/kg/16D-I
TOXIC EFFECTS :
Related to Chronic Data - death
REFERENCE :
NTPTR* National Toxicology Program Technical Report Series. (Research Triangle Park, NC 27709) No.206- Volume(issue)/page/year: NTP-TR-423,1993
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
19500 mg/kg/13W-I
TOXIC EFFECTS :
Liver - other changes Blood - changes in erythrocyte (RBC) count Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - true cholinesterase
REFERENCE :
NTPTR* National Toxicology Program Technical Report Series. (Research Triangle Park, NC 27709) No.206- Volume(issue)/page/year: NTP-TR-423,1993
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
27 gm/kg/16D-I
TOXIC EFFECTS :
Related to Chronic Data - death
REFERENCE :
NTPTR* National Toxicology Program Technical Report Series. (Research Triangle Park, NC 27709) No.206- Volume(issue)/page/year: NTP-TR-423,1993
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
104 gm/kg/13W-I
TOXIC EFFECTS :
Liver - changes in liver weight Related to Chronic Data - death
REFERENCE :
NTPTR* National Toxicology Program Technical Report Series. (Research Triangle Park, NC 27709) No.206- Volume(issue)/page/year: NTP-TR-423,1993 ** TUMORIGENIC DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
433 gm/kg/2Y-I
TOXIC EFFECTS :
Tumorigenic - neoplastic by RTECS criteria Kidney, Ureter, Bladder - Kidney tumors
REFERENCE :
NTPTR* National Toxicology Program Technical Report Series. (Research Triangle Park, NC 27709) No.206- Volume(issue)/page/year: NTP-TR-423,1993
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
144 gm/kg/2Y-I
TOXIC EFFECTS :
Tumorigenic - neoplastic by RTECS criteria Liver - tumors
REFERENCE :
NTPTR* National Toxicology Program Technical Report Series. (Research Triangle Park, NC 27709) No.206- Volume(issue)/page/year: NTP-TR-423,1993 *** REVIEWS *** TOXICOLOGY REVIEW PMDCAY Progress in Medical Chemistry. (Elsevier Science Pub. Co., Inc., 52 Vanderbilt Ave., New York, NY 10017) V.1- 1961- Volume(issue)/page/year: 10,85,1974 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 83169 No. of Facilities: 21 (estimated) No. of Industries: 1 No. of Occupations: 2 No. of Employees: 456 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 83169 No. of Facilities: 65 (estimated) No. of Industries: 3 No. of Occupations: 8 No. of Employees: 2054 (estimated) No. of Female Employees: 276 (estimated)
Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H302-H315-H319-H335
Precautionary Statements P261-P305 + P351 + P338
Personal Protective Equipment Eyeshields;Faceshields;full-face respirator (US);Gloves;multi-purpose combination respirator cartridge (US);type ABEK (EN14387) respirator filter
Hazard Codes Xn:Harmful;
Risk Phrases R22;R36/37/38
Safety Phrases S26-S36
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS MW5775000
HS Code 29322980
HS Code 2932209090
Summary 2932209090. other lactones. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%
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