tetrahydro-3,4-dipiperonylfuran-2-ol

CAS: 18423-69-3 C20 H20 O6 MW: 356.37460000

Identification

Namecubebin
IUPAC(2S,3R,4R)-3,4-bis(1,3-benzodioxol-5-ylmethyl)oxolan-2-ol
CAS Number18423-69-3
EINECS242-300-6
FDA UNIIJ237078S8A
Molecular FormulaC20 H20 O6
Molecular Weight356.37460000
Nikkaji NumberJ941.075I

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 ToxicityNot determined
Dermal ToxicityNot determined
Inhalation ToxicityNot determined

GHS Classification

['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']

Safety in Use

Categorynatural substances and extractives
Recommendation for cubebin usage levels up tonot for fragrance use.
Recommendation for cubebin flavor usage levels up tonot for flavor use.

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Potential Uses

None Found

Natural Occurrence

cubeb pepper black pepper fruit pepper black pepper leaf

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].