ambrosin
3,3a,4,5,6,6a,9a,9b-octahydro-6,9a-dimethyl-3-methyleneazuleno(4,5b)furan-2,9-dione
Identification
| Name | ambrosin |
| IUPAC | (3aS,6S,6aR,9aR,9bR)-6,9a-dimethyl-3-methylidene-3a,4,5,6,6a,9b-hexahydroazuleno[8,7-b]furan-2,9-dione |
| CAS Number | 509-93-3 |
| FDA UNII | 6XI048644B |
| Molecular Formula | C15 H18 O3 |
| Molecular Weight | 246.30606000 |
| Nikkaji Number | J10.275J |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 146.00 °C. @ 760.00 mm Hg |
| Boiling Point | 418.00 to 419.00 °C. @ 760.00 mm Hg (est), 146.00 °C. @ 760.00 mm Hg |
| Flash Point | 369.00 °F. TCC ( 187.30 °C. ) (est) |
| logP (o/w) | 1.030 |
| Soluble in | water, 3271 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for ambrosin usage levels up to | not for fragrance use. |
| Recommendation for ambrosin flavor usage levels up to | not for flavor use. |
No supplier data available
Potential Uses
Natural Occurrence
Synonyms
10aH-
ambrosa-2,11(13)-dien-12-oic acid, 6β-hydroxy-4-oxo-, g-lactone
azuleno[4,5-b]furan-2,9-dione, 3,3a,4,5,6,6a,9a,9b-octahydro-6,9a-dimethyl-3-methylene-, (3aS,6S,6aR,9aR,9bR)-
azuleno[4,5-b]furan-2,9-dione, 3,3a,4,5,6,6a,9a,9b-octahydro-6,9a-dimethyl-3-methylene-, (3aS,6S,6aR,9aR)-
(3aS,6S,6aR,9aR,9bR)-6,9a-
dimethyl-3-methylene-3,3a,4,5,6,6a-hexahydroazuleno[4,5-b]furan-2,9(9aH,9bH)-dione
(3aS,6S,6aR,9aR,9bR)-6,9a-
dimethyl-3-methylidene-3,3a,4,5,6,6a,9a,9b-octahydroazuleno[4,5-b]furan-2,9-dione
(3aS,6S,6aR,9aR,9bR)-6,9a-
dimethyl-3-methylidene-3a,4,5,6,6a,9b-hexahydroazuleno[8,7-b]furan-2,9-dione
6b-
hydroxy-4-oxo-10aH-ambrosa-2,11(13)-dien-12-oic acid g-lactone
3,3a,4,5,6,6a,9a,9b-
octahydro-6,9a-dimethyl-3-methylene azuleno(4,5b)furan-2,9-dione
3,3a,4,5,6,6a,9a,9b-
octahydro-6,9a-dimethyl-3-methyleneazuleno(4,5b)furan-2,9-dione
PubMed:
Anti-cancer stem cell activity of a sesquiterpene lactone isolated from Ambrosia arborescens and of a synthetic derivative.
PubMed:
Potassium increases the antitumor effects of ascorbic acid in breast cancer cell lines in vitro.
PubMed:
Cytotoxicity of 35 medicinal plants from Sudan towards sensitive and multidrug-resistant cancer cells.
PubMed:
Astrocytes produce dendritic cell-attracting chemokines in vitro and in multiple sclerosis lesions.
PubMed:
Chemokines and glial cells: a complex network in the central nervous system.
PubMed:
Cell cycle regulation by p38 MAP kinases.
PubMed:
Cytotoxic sesquiterpene lactones mediate their death-inducing effect in leukemia T cells by triggering apoptosis.
PubMed:
Cyclic GMP inhibition of metabotropic glutamate receptor-induced phosphoinositide hydrolysis in mesencephalic neurons.
PubMed:
Synthesis and cytotoxicity of water-soluble ambrosin prodrug candidates.
PubMed:
The effect of Ambrosia maritima (Damsissa) on the viability of Lymnaea cailliaudi; an experimental study.
PubMed:
pH-dependent lipid packing, membrane permeability and fusion in phosphatidylcholine vesicles.
PubMed:
Toxicity and mutagenicity of the molluscicidal plant Ambrosia maritima L.
PubMed:
Activation of latent K+ uniport in mitochondria treated with the ionophore A23187.
PubMed:
Ambrosia maritima a larvicide and pupacide for Anopheles pharoensis ambrosin as an effective insecticide. I. Laboratory experimentation.
PubMed:
The molluscicidal properties of Ambrosia maritima L. (compositae). 1. Design for a molluscicide field trial.
PubMed:
[Parthenium hysterophorus allergy. A weed problem in India (author's transl)].
PubMed:
Contact hypersensitivity to sesquiterpene lactones in Chyrsanthemum dermatitis.
PubMed:
The molluscicidal properties of natural products from Ambrosia maritima.
PubMed:
Ambrosin, tumor inhibitory agent from Hymenoclea salsola (Asteraceae).
PubMed:
The chemistry of Ambrosia maritima L. II. Hydrogenation, oxidation, and dehydrogenation of ambrosin and damsin.
PubMed:
The chemistry of Ambrosia maritima L. I. The isolation and preliminary characterization of ambrosin and damsin.