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

terrein
2-cyclopenten-1-one, 4,5-dihydroxy-3-(1-propenyl)-, (4S-(3(E),4alpha,5beta))- (9CI)

Supplier Sponsors

Name:(4S,5R)-4,5-dihydroxy-3-[(E)-prop-1-enyl]cyclopent-2-en-1-one
CAS Number: 582-46-7Picture of molecule3D/inchi
FDA UNII: 3I47HPE16N
Nikkaji Web:J16.229I
XlogP3-AA:-0.60 (est)
Molecular Weight:154.16530000
Formula:C8 H10 O3
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:cosmetic ingredient for skin conditioning
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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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
Soluble in:
 water, 4035 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
CosIng:cosmetic data
Cosmetic Uses: skin conditioning
 
Suppliers:
BOC Sciences
For experimental / research use only.
Terrein >95% by HPLC
Odor: characteristic
Use: A polar, substituted dihydrocyclopentenone; reduces melanin synthesis by reducing tyrosinase production via ERK activation, followed by MITF down-regulation; also reduces human keratinocyte proliferation by inhibiting ERK and by decreasing the expression
Glentham Life Sciences
Terrein
Sigma-Aldrich: Sigma
For experimental / research use only.
Terrein from Aspergillus terreus, ≥98% (HPLC)
sds
 
Safety Information:
Preferred SDS: View
 
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:
cosmetic ingredient for skin conditioning
Recommendation for terrein usage levels up to:
 not for fragrance use.
 
Recommendation for terrein 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 :6436830
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
(4S,5R)-4,5-dihydroxy-3-[(E)-prop-1-enyl]cyclopent-2-en-1-one
Chemidplus:0000582467
 
References:
 (4S,5R)-4,5-dihydroxy-3-[(E)-prop-1-enyl]cyclopent-2-en-1-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):6436830
Pubchem (sid):135057978
 
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
CHEMBL:View
HMDB (The Human Metabolome Database):Search
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 found in nature
 
Synonyms:
2-cyclopenten-1-one, 4,5-dihydroxy-3-(1-propenyl)-
2-cyclopenten-1-one, 4,5-dihydroxy-3-(1-propenyl)-, (4S-(3(E),4alpha,5beta))- (9CI)
2-cyclopenten-1-one, 4,5-dihydroxy-3-[(1E)-1-propen-1-yl]-, (4S,5R)-
2-cyclopenten-1-one, 4,5-dihydroxy-3-propenyl- (8CI)
(4S-(3(E),4alpha,5beta))-4,5-dihydroxy-3-(1-propenyl)-2-cyclopenten-1-one
4,5-dihydroxy-3-(1-propenyl)-2-cyclopenten-1-one
(4S,5R)-4,5-dihydroxy-3-[(E)-prop-1-enyl]cyclopent-2-en-1-one
 

Articles:

PubMed:Modification of artificial sea water for the mass production of (+)-terrein by Aspergillus terreus strain PF26 derived from marine sponge Phakellia fusca.
PubMed:How to trigger a fungal weapon.
PubMed:Phytotoxin production in Aspergillus terreus is regulated by independent environmental signals.
PubMed:A new high-performance heterologous fungal expression system based on regulatory elements from the Aspergillus terreus terrein gene cluster.
PubMed:(+)‑Terrein inhibits human hepatoma Bel‑7402 proliferation through cell cycle arrest.
PubMed:The marine-derived fungal metabolite, terrein, inhibits cell proliferation and induces cell cycle arrest in human ovarian cancer cells.
PubMed:Synthetic (+)-terrein suppresses interleukin-6/soluble interleukin-6 receptor induced-secretion of vascular endothelial growth factor in human gingival fibroblasts.
PubMed:Promiscuity breeds diversity: the role of polyketide synthase in natural product biosynthesis.
PubMed:Terrein biosynthesis in Aspergillus terreus and its impact on phytotoxicity.
PubMed:Culture-based and sequence-based insights into biosynthesis of secondary metabolites by Aspergillus terreus ATCC 20542.
PubMed:Terrein induces apoptosis in HeLa human cervical carcinoma cells through p53 and ERK regulation.
PubMed:Enhanced production of (+)-terrein in fed-batch cultivation of Aspergillus terreus strain PF26 with sodium citrate.
PubMed:A new β-glucuronidase inhibiting butyrolactone from the marine endophytic fungus Aspergillus terreus.
PubMed:Operating conditions optimization for (+)-terrein production in a stirred bioreactor by Aspergillus terreus strain PF-26 from marine sponge Phakellia fusca.
PubMed:Asperjinone, a nor-neolignan, and terrein, a suppressor of ABCG2-expressing breast cancer cells, from thermophilic Aspergillus terreus.
PubMed:Three new compounds from Aspergillus terreus PT06-2 grown in a high salt medium.
PubMed:Aspergillus sect. Aeni sect. nov., a new section of the genus for A.karnatakaensis sp. nov. and some allied fungi.
PubMed:Enhancement of osteoblast biocompatibility on titanium surface with Terrein treatment.
PubMed:Long-term suppression of tyrosinase by terrein via tyrosinase degradation and its decreased expression.
PubMed:Aspernolides A and B, butenolides from a marine-derived fungus Aspergillus terreus.
PubMed:Four new species of Emericella from the Mediterranean region of Europe.
PubMed:A new terrein glucoside, a novel inhibitor of angiogenin secretion in tumor angiogenesis.
PubMed:Rapid analysis of fungal cultures and dried figs for secondary metabolites by LC/TOF-MS.
PubMed:Terrein reduces pulpal inflammation in human dental pulp cells.
PubMed:The hypopigmentary action of KI-063 (a new tyrosinase inhibitor) combined with terrein.
PubMed:Weed growth inhibitors from Aspergillus fischeri TISTR 3272.
PubMed:Terrein inhibits keratinocyte proliferation via ERK inactivation and G2/M cell cycle arrest.
PubMed:Production of mycotoxins by Aspergillus lentulus and other medically important and closely related species in section Fumigati.
PubMed:Terrein, a fungal metabolite, inhibits the epidermal proliferation of skin equivalents.
PubMed:Polyphasic taxonomy of Aspergillus fumigatus and related species.
PubMed:Emericella venezuelensis, a new species with stellate ascospores producing sterigmatocystin and aflatoxin B1.
PubMed:Synthesis and melanin biosynthesis inhibitory activity of (+/-)-terrein produced by Penicillium sp. 20135.
PubMed:Terrein: a new melanogenesis inhibitor and its mechanism.
PubMed:Bioactive metabolites from a marine-derived strain of the fungus Emericella variecolor.
PubMed:Characterization of stereochemistry and molecular conformation using solid-state NMR tensors.
PubMed:Gas chromatographic analysis of the mycotoxins kojic acid, terreic acid, and terrein.
PubMed:Studies in the biochemistry of micro-organisms: The molecular constitution of terrein, a metabolic product of Aspergillus terreus Thom.
PubMed:Studies in the biochemistry of micro-organisms: The metabolic products of Aspergillus terreus Thom. A new mould metabolic product-terrein.
 
Notes:
None found
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