cubebin
tetrahydro-3,4-dipiperonylfuran-2-ol
Identification
| Name | cubebin |
| IUPAC | (2S,3R,4R)-3,4-bis(1,3-benzodioxol-5-ylmethyl)oxolan-2-ol |
| CAS Number | 18423-69-3 |
| EINECS | 242-300-6 |
| FDA UNII | J237078S8A |
| Molecular Formula | C20 H20 O6 |
| Molecular Weight | 356.37460000 |
| Nikkaji Number | J941.075I |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Melting Point | 131.50 °C. @ 760.00 mm Hg |
| Boiling Point | 526.80 °C. @ 760.00 mm Hg (est) |
| Flash Point | 522.00 °F. TCC ( 272.40 °C. ) (est) |
| logP (o/w) | 3.340 (est) |
| Soluble in | water, 11 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 cubebin usage levels up to | not for fragrance use. |
| Recommendation for cubebin flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
3,4-bis(1,3-
benzodioxol-5-yl methyl) tetrahydro-2-furanol
(2S,3R,4R)-3,4-bis(1,3-
benzodioxol-5-ylmethyl)oxolan-2-ol
2-
furanol, 3,4-bis(1,3-benzodioxol-5-ylmethyl)tetrahydro-
tetrahydro-3,4-dipiperonyl furan-2-ol
tetrahydro-3,4-dipiperonylfuran-2-ol
PubMed:
The lignan (-)-hinokinin displays modulatory effects on human monoamine and GABA transporter activities.
PubMed:
A comparative study of the modulatory effects of (-)-cubebin on the mutagenicity/recombinogenicity induced by different chemical agents.
PubMed:
The lignan (-)-cubebin inhibits vascular contraction and induces relaxation via nitric oxide activation in isolated rat aorta.
PubMed:
Evaluation of the in vivo therapeutic properties of (-)-cubebin and (-)-hinokinin against Trypanosoma cruzi.
PubMed:
Mutagenicity and antimutagenicity of (-)-hinokinin a trypanosomicidal compound measured by Salmonella microsome and comet assays.
PubMed:
In vivo infection by Trypanosoma cruzi: a morphometric study of tissue changes in mice.
PubMed:
Antiprotozoal and Antimycobacterial Activities of Pure Compounds from Aristolochia elegans Rhizomes.
PubMed:
Antioxidant capacity and larvicidal and antifungal activities of essential oils and extracts from Piper krukoffii.
PubMed:
The effect of the dibenzylbutyrolactolic lignan (-)-cubebin on doxorubicin mutagenicity and recombinogenicity in wing somatic cells of Drosophila melanogaster.
PubMed:
Genotoxic effects of (-)-cubebin in somatic cells of mice.
PubMed:
Trypanosoma cruzi: evaluation of (-)-cubebin derivatives activity in the messenger RNAs processing.
PubMed:
Effect of the dibenzylbutyrolactone lignan (-)-hinokinin on doxorubicin and methyl methanesulfonate clastogenicity in V79 Chinese hamster lung fibroblasts.
PubMed:
Reduction of parasitism tissue by treatment of mice chronically infected with Trypanosoma cruzi with lignano lactones.
PubMed:
Antitumor-promoting activity of lignans: inhibition of human cytomegalovirus IE gene expression.
PubMed:
Antimycobacterial activity of natural and semi-synthetic lignans.
PubMed:
Histamine release inhibitory activity of Piper nigrum leaf.
PubMed:
Cubebin and derivatives as inhibitors of mitochondrial complex I. Proposed interaction with subunit B8.
PubMed:
Chemical constituents of Aristolochia constricta: antispasmodic effects of its constituents in guinea-pig ileum and isolation of a diterpeno-lignan hybrid.
PubMed:
Evaluation of insecticidal activity of diterpenes and lignans from Aristolochia malmeana against Anticarsia gemmatalis.
PubMed:
Piper cubeba targets multiple aspects of the androgen-signalling pathway. A potential phytotherapy against prostate cancer growth?
PubMed:
Testosterone 5alpha-reductase inhibitory active constituents of Piper nigrum leaf.
PubMed:
Mechanism of the melanogenesis stimulation activity of (-)-cubebin in murine B16 melanoma cells.
PubMed:
New calamenene sesquiterpenes from Tarenna madagascariensis.
PubMed:
Evaluation of piper cubeba extract, (-)-cubebin and its semi-synthetic derivatives against oral pathogens.
PubMed:
(-)-Hinokinin causes antigenotoxicity but not genotoxicity in peripheral blood of Wistar rats.
PubMed:
In vitro and in vivo activity of lignan lactones derivatives against Trypanosoma cruzi.
PubMed:
Configurational analysis of cubebins and bicubebin from Aristolochia lagesiana and Aristolochia pubescens.
PubMed:
Lignans from cell suspension cultures of Phyllanthus niruri, an Indonesian medicinal plant.
PubMed:
Synthesis and biological activity evaluation of lignan lactones derived from (-)-cubebin.
PubMed:
Trypanocidal activity of (-)-cubebin derivatives against free amastigote forms of Trypanosoma cruzi.
PubMed:
Melanogenesis stimulation in murine B16 melanoma cells by Piper nigrum leaf extract and its lignan constituents.
PubMed:
Analgesic and anti-inflammatory activities of (-)-o benzyl cubebin, a (-)-cubebin derivative, obtained by partial synthesis.
PubMed:
Insecticidal activity of chemical constituents from Aristolochia pubescens against Anticarsia gemmatalis larvae.
PubMed:
Analgesic and anti-inflammatory activities evaluation of (-)-O-acetyl, (-)-O-methyl, (-)-O-dimethylethylamine cubebin and their preparation from (-)-cubebin.
PubMed:
Anti-inflammatory activity of cubebin, a lignan from the leaves of Zanthoxyllum naranjillo Griseb.
PubMed:
Analgesic activity of the lignans from Lychnophora ericoides.
PubMed:
Evaluation of the trypanocidal activity of lignans isolated from the leaves of Zanthoxylum naranjillo.
PubMed:
A New Linalool Derivative and Other Constituents from Piper ribesoides.
PubMed:
[Constituents of Aristolochia triangularis].
PubMed:
[Notice on the structure of cubebin].