catalpalactone, 1585-68-8

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CODE148693 CODE148693
Product(s):
1585-68-8 Catalpalactone
Catalpalactone isolated from the wood of Catalpa ovata. It inhibited dopamine biosynthesis by reducing TH and AADC activities and enhanced L-DOPA-induced cytotoxiciy in PC12 cells.

Name:	3-(2,2-dimethyl-6-oxo-3H-pyran-5-yl)-3H-2-benzofuran-1-one
CAS Number:	1585-68-8	3D/inchi
Other(deleted CASRN):	133591-03-4
FDA UNII:	P61GH0V29Z
Nikkaji Web:	J13.166K
XlogP3-AA:	2.40 (est)
Molecular Weight:	258.27338000
Formula:	C15 H14 O4
BioActivity Summary:	listing
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
Boiling Point:	467.10 °C. @ 760.00 mm Hg (est)
Flash Point:	473.00 °F. TCC ( 245.20 °C. ) (est)
logP (o/w):	2.050 (est)
Soluble in:
	water, 2022 mg/L @ 25 °C (est)

Organoleptic Properties:

Odor and/or flavor descriptions from others (if found).

Cosmetic Information:

None found

Suppliers:

BOC Sciences

For experimental / research use only.

Catalpalactone

Odor: characteristic

Use: Catalpalactone isolated from the wood of Catalpa ovata. It inhibited dopamine biosynthesis by reducing TH and AADC activities and enhanced L-DOPA-induced cytotoxiciy in PC12 cells.

Coompo

For experimental / research use only.

Catalpalactone from Plants ≥96%

Odor: characteristic

Use: The effects of catalpalactone on dopamine biosynthesis and L-DOPA-induced cytotoxicity in PC12 cells were investigated. Catalpalactone at 5-30�M decreased intracellular dopamine content with the IC(50) value of 22.1�M. Catalpalactone at 5-20�M, but not 30�M, did not alter cell viability. Catalpalactone at 20�M inhibited tyrosine hydroxylase (TH) and aromatic-l-amino acid decarboxylase (AADC) activities. Catalpalactone also decreased cyclic AMP levels and inhibited TH phosphorylation. In addition, catalpalactone at 20�M reduced the increases in dopamine levels induced by L-DOPA (20-50�M). Catalpalactone (5-30�M) associated with L-DOPA (50-100�M) enhanced L-DOPA-induced cytotoxicity at 48h, which was prevented by N-acetyl-l-cysteine. These results suggest that catalpalactone inhibited dopamine biosynthesis by reducing TH and AADC activities and enhanced L-DOPA-induced cytotoxiciy in PC12 cells.

Safety Information:


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:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in Use Information:

Category:
natural substances and extractives
Recommendation for catalpalactone usage levels up to:
	not for fragrance use.

Recommendation for catalpalactone flavor usage levels up to:
	not for flavor use.

Safety References:

EPI System: View

AIDS Citations:Search

Cancer Citations:Search

Toxicology Citations:Search

EPA ACToR:Toxicology Data

EPA Substance Registry Services (SRS):Registry

Laboratory Chemical Safety Summary :3014018

National Institute of Allergy and Infectious Diseases:Data

3-(2,2-dimethyl-6-oxo-3H-pyran-5-yl)-3H-2-benzofuran-1-one

Chemidplus:0001585688

References:

	3-(2,2-dimethyl-6-oxo-3H-pyran-5-yl)-3H-2-benzofuran-1-one
NIST Chemistry WebBook:	Search Inchi
Pubchem (cid):	3014018
Pubchem (sid):	135205113

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):	C16929
HMDB (The Human Metabolome Database):	Search
VCF-Online:	VCF Volatile Compounds in Food
ChemSpider:	View
Wikipedia:	View
EFSA Update of results on the monitoring of furan levels in food:	Read Report
EFSA Previous report: Results on the monitoring of furan levels in food:	Read Report
EFSA Report of the CONTAM Panel on provisional findings on furan in food:	Read Report

Potential Blenders and core components note

None Found

Potential Uses:

None Found

Occurrence (nature, food, other):note

found in nature

Synonyms:

1(3H)-iso	benzofuranone, 3-(5,6-dihydro-6,6-dimethyl-2-oxo-2H-pyran-3-yl)-
3-(5,6-	dihydro-6,6-dimethyl-2-oxo-2H-pyran-3-yl)-1(3H)-isobenzofuranone
3-(6,6-	dimethyl-2-oxo-5,6-dihydro-2H-pyran-3-yl)-2-benzofuran-1(3H)-one
3-(2,2-	dimethyl-6-oxo-3H-pyran-5-yl)-3H-2-benzofuran-1-onee

Articles:

PubMed:Naphthoquinones from Catalpa ovata and their inhibitory effects on the production of nitric oxide.

PubMed:Effects of catalpalactone on dopamine biosynthesis and L-DOPA-induced cytotoxicity in PC12 cells.

PubMed:Antitumor-promoting naphthoquinones from Catalpa ovata.

PubMed:Major antitermitic components of the heartwood of southern catalpa.

PubMed:Structure of catalpalactone, a new phthalide from Catalpa wood.

PubMed:The structure of catalpalactone.

Notes:

None found

catalpalactone 3-(5,6-dihydro-6,6-dimethyl-2-oxo-2H-pyran-3-yl)-1(3H)-isobenzofuranone

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Articles:

catalpalactone
3-(5,6-dihydro-6,6-dimethyl-2-oxo-2H-pyran-3-yl)-1(3H)-isobenzofuranone