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cytochalasin C

natural substances and extractives
2D:
3D:
CAS Number: 22144-76-9
ECHA EC Number: 244-803-6
FDA UNII: Search
Category: natural substances and extractives
IUPAC Name: cytochalasin C
InChI : InChI=1/C30H37NO6/c1-17-10-9-13-22-26(33)19(3)18(2)25-23(16-21-11-7-6-8-12-21)31-28(35)30(22,25)24(37-20(4)32)14-15-29(5,36)27(17)34/h6-9,11-15,17,22-26,33,36H,10,16H2,1-5H3,(H,31,35)/b13-9-,15-14-/t17-,22-,23?,24+,25?,26+,29+,30+/m0/s1
Std.InChI: InChI=1S/C30H37NO6/c1-17-10-9-13-22-26(33)19(3)18(2)25-23(16-21-11-7-6-8-12-21)31-28(35)30(22,25)24(37-20(4)32)14-15-29(5,36)27(17)34/h6-9,11-15,17,22-26,33,36H,10,16H2,1-5H3,(H,31,35)/b13-9-,15-14-/t17-,22-,23?,24+,25?,26+,29+,30+/m0/s1
InChIKey : NAIODHJWOHMDJX-RPTVSDKTBY
Std.InChIKey: NAIODHJWOHMDJX-RPTVSDKTSA-N
SMILES : O=C1NC([C@@H]3\C(=C(/[C@@H](O)[C@@H]2\C=C/C[C@@H](C(=O)[C@](O)(\C=C/[C@@H](OC(=O)C)[C@]123)C)C)C)C)Cc4ccccc4
MDL: MFCD00066080
Molar Refractivity : 139.45 ± 0.5 cm3 (est)
Parachor : 1052.9 ± 8.0 cm3 (est)
Index of Refraction : 1.605 ± 0.05 (est)
Surface Tension : 45.7 ± 7.0 dyne/cm (est)
Density : 1.25 ± 0.1 g/cm3 (est)
Polarizability : 55.28 ± 0.5 10-24cm3 (est)

US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:

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Pubchem Patents:Search
PubMed:Search
NCBI:Search

Physical Properties:

Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 714.32 °C. @ 760.00 mm Hg (est)
Flash Point: 726.00 °F. TCC ( 385.80 °C. ) (est)
logP (o/w): 3.250 (est)
Soluble in:
water, 0.2403 mg/L @ 25 °C (est)

Cosmetic Information:

None found

Suppliers:

BOC Sciences
For experimental / research use only.
Cytochalasin C >99% by HPLC
Odor: characteristic
Use: One of a family of potent mycotoxins produced by a range of fungi; exhibit profound effects on cytoskeletal proteins, resulting in pronounced morphogenic changes in animals and plants
ExtraSynthese
For experimental / research use only.
Cytochalasin C
Santa Cruz Biotechnology
For experimental / research use only.
Cytochalasin C >99%
Sigma-Aldrich: Sigma
For experimental / research use only.
Cytochalasin C from Metarrhizium anisopliae ≥97.0% (TLC)

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:
intraperitoneal-mouse LD > 100 mg/kg
Chemical and Pharmaceutical Bulletin. Vol. 21, Pg. 2268, 1973.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined

Safety in Use Information:

Category:
natural substances and extractives
Recommendation for cytochalasin C usage levels up to:
not for fragrance use.
Recommendation for cytochalasin C 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 :6440868
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
Chemidplus:0022144769
RTECS:HA5300500 for cas# 22144-76-9

References:

NIST Chemistry WebBook:Search Inchi
Pubchem (cid):6440868
Pubchem (sid):135116036

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
HMDB (The Human Metabolome Database):Search
Export Tariff Code:2933.79.1000
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View

Potential Blenders and core components :

None Found

Potential Uses:

None Found

Occurrence (nature, food, other):

found in nature

Synonyms:

1H-cycloundec(d)isoindole-1,11(2H)-dione, 3-benzyl-3,3a,6,6a,9,10,12,15-octahydro-6,12,15-trihydroxy-4,5,10,12-tetramehtyl-, 15-acetate
7(S),18-dihydroxy-16(S),18(R)-dimethyl-10-phenyl(11)cytochalasa-5,13(E),19(E)-triene-1,17-dione 21(R)-acetate

Articles:

PubMed:[Secondary metabolites of mangrove endophytic fungus BL321 in the South China Sea].
PubMed:TCR/CD28-stimulated actin dynamics are required for NFAT1-mediated transcription of c-rel leading to CD28 response element activation.
PubMed:In vitro inhibition of human neutrophil histotoxicity by ambroxol: evidence for a multistep mechanism.
PubMed:[Morphological and functional changes of tissue receptors of an organ plexus under the effect of blockers of cytoskeleton assembly].
PubMed:Cytoskeleton regulates expression of genes for transforming growth factor-beta 1 and extracellular matrix proteins in dermal fibroblasts.
PubMed:Evidence for LFA-1/ICAM-1 dependent stimulation of protein tyrosine phosphorylation in human B lymphoid cell lines during homotypic adhesion.
PubMed:Alteration in cell morphology triggers transforming growth factor-beta 1, collagenase, and tissue inhibitor of metalloproteinases-I expression in normal and hypertrophic scar fibroblasts.
PubMed:Phenotype modulation in primary cultures of rat aortic smooth muscle cells. Effects of drugs that interfere with the functions of the vacuolar system and the cytoskeleton.
PubMed:Actin assembly activity of cytochalasins and cytochalasin analogs assayed using fluorescence photobleaching recovery.
PubMed:Inhibitory effect of cytochalasins on the motility of rat epididymal spermatozoa in vitro.
PubMed:The ultrastructural changes of S-100 protein localization during lipolysis in adipocytes. An immunoelectron-microscopic study.
PubMed:Effect of cytochalasins on surfactant release from alveolar type II cells.
PubMed:Superoxide generation by neonatal and adult rabbit alveolar macrophages.
PubMed:Functional studies on B cell hybridomas with B cell surface antigens. IV. Direct effects of cytochalasin B on differentiation.
PubMed:Structure-activity correlations of cytochalasins. Novel halogenated and related cytochalasin C and D derivatives.
PubMed:Correlation between effects of 24 different cytochalasins on cellular structures and cellular events and those on actin in vitro.
PubMed:Stimulation of actin ATPase activity by cytochalasins provides evidence for a new species of monomeric actin.
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