EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

cubebin
tetrahydro-3,4-dipiperonylfuran-2-ol

Supplier Sponsors

Name:(2S,3R,4R)-3,4-bis(1,3-benzodioxol-5-ylmethyl)oxolan-2-ol
CAS Number: 18423-69-3Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg:242-300-6
FDA UNII: J237078S8A
Nikkaji Web:J941.075I
XlogP3-AA:3.40 (est)
Molecular Weight:356.37460000
Formula:C20 H20 O6
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
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)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
BOC Sciences
For experimental / research use only.
Cubebin
 
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 cubebin usage levels up to:
 not for fragrance use.
 
Recommendation for cubebin 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 :117443
National Institute of Allergy and Infectious Diseases:Data
(2S,3R,4R)-3,4-bis(1,3-benzodioxol-5-ylmethyl)oxolan-2-ol
Chemidplus:0018423693
 
References:
 (2S,3R,4R)-3,4-bis(1,3-benzodioxol-5-ylmethyl)oxolan-2-ol
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):117443
Pubchem (sid):135075766
 
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):C10549
HMDB (The Human Metabolome Database):HMDB30682
FooDB:FDB002600
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
 cubeb
Search Trop Picture
 pepper black pepper fruit
Search Trop Picture
 pepper black pepper leaf
Search Trop Picture
 
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
 

Articles:

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].
 
Notes:
Isol. from unripe fruit of Piper cubeba (cubeb pepper) About 15% of a volatile oil is obtained by distilling cubebs with water. Cubebene, the liquid portion, has the formula C15H24. It is a pale green or blue-yellow viscous liquid with a warm woody, slightly camphoraceous odor. After rectification with water, or on keeping, this deposits rhombic crystals of camphor of cubebs.; Cubeb (Piper cubeba), or tailed pepper, is a plant in genus Piper, cultivated for its fruit and essential oil. It is mostly grown in Java and Sumatra, hence sometimes called Java pepper. The fruits are gathered before they are ripe, and carefully dried. Commercial cubebs consist of the dried berries, similar in appearance to black pepper, but with stalks attached ? the "tails" in "tailed pepper". The dried pericarp is wrinkled, its color ranges from grayish-brown to black. The seed is hard, white and oily. The odor of cubebs is described as agreeable and aromatic. The taste, pungent, acrid, slightly bitter and persistent. It has been described as tasting like allspice, or like a cross between allspice and black pepper.; Cubebin (C10H10O3) is a crystalline substance existing in cubebs, discovered by Eugène Soubeiran and Capitaine in 1839. It may be prepared from cubebene, or from the pulp left after the distillation of the oil. The drug, along with gum, fatty oils, and malates of magnesium and calcium, contains also about 1% of cubebic acid, and about 6% of a resin. The dose of the fruit is 30 to 60 grains, and the British Pharmacopoeia contains a tincture with a dose of 4 to 1 dram.; In Europe, cubeb was one of the valuable spices during the Middle Ages. It was ground as a seasoning for meat or used in sauces. A medieval recipe includes cubeb in making sauce sarcenes, which consists of almond milk and several spices. As an aromatic confectionery, cubeb was often candied and eaten whole.; In traditional Chinese medicine cubeb is used for its alleged warming property. In Tibetan medicine, cubeb (ka ko la in Tibetan) is one of bzang po drug, six fine herbs beneficial to specific organs in the body, with cubeb assigned to the spleen.
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