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I1279

Sigma-Aldrich

Isovelleral

solid

Synonym(s):

(+)-Isovelleral

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About This Item

Empirical Formula (Hill Notation):
C15H20O2
CAS Number:
37841-91-1
Molecular Weight:
232.32
MDL number:
MFCD01735881
UNSPSC Code:
12352200
PubChem Substance ID:
24895926

form

solid

color

white

solubility

H2O: insoluble
organic solvents: soluble

shipped in

dry ice

storage temp.

−20°C

SMILES string

[H]C(=O)C1=C[C@]2([H])CC(C)(C)C[C@]2([H])[C@]3(C)C[C@@]13C([H])=O

InChI

1S/C15H20O2/c1-13(2)5-10-4-11(7-16)15(9-17)8-14(15,3)12(10)6-13/h4,7,9-10,12H,5-6,8H2,1-3H3/t10-,12+,14-,15-/m1/s1

InChI key

PJAAESPGJOSQGZ-DZGBDDFRSA-N

Biochem/physiol Actions

Vanilloid receptor agonist.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Precautionary Statements

P261 - P305 + P351 + P338

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Isabelle Aujard et al.
Bioorganic & medicinal chemistry, 13(22), 6145-6150 (2005-08-02)
The synthesis and in vitro cytotoxicity toward various tumor cell lines of (+/-)-tridemethylisovelleral, an analogue of the bioactive fungal sesquiterpene (+)-isovelleral retaining the bicyclo[4,1,0]hept-2-en-1,2-dicarbaldehyde system but lacking the three methyl groups, is reported. The cytotoxicity of tridemethylisovelleral toward several tumor
M Jonassohn et al.
Acta chemica Scandinavica (Copenhagen, Denmark : 1989), 49(7), 530-535 (1995-07-01)
The autoxidation of the two mutagenic and antimicrobial sesquiterpenes merulidial (1a) and isovelleral (5) generates a number of bioactive products that are suggested to be partly responsible for the mutagenic and antimicrobial activities of the two compounds. The biological activities
D Smart et al.
European journal of pharmacology, 417(1-2), 51-58 (2001-04-13)
A full pharmacological characterisation of the recently cloned human vanilloid VR1 receptor was undertaken. In whole-cell patch clamp studies, capsaicin (10 microM) elicited a slowly activating/deactivating inward current in human embryonic kidney (HEK293) cells stably expressing human vanilloid VR1 receptor
A Forsby et al.
Neuroscience letters, 217(1), 50-54 (1996-10-11)
The pungent sesquiterpenoid unsaturated dialdehydes polygodial and isovelleral, have previously been shown to increase the intracellular free calcium concentration [Ca2+]i in human neuroblastoma SH-SY5Y cells, partly by a release from intracellular Ca2+ stores, whereas the non-pungent compound epipolygodial, had no
R P Bell et al.
The Journal of organic chemistry, 66(7), 2350-2357 (2001-04-03)
A general and efficient route to the marasmane skeleton is described. Total syntheses of two simple marasmanes (35 and 37) in racemic form were achieved using a MgI2-catalyzed rearrangement-cyclopropanation reaction of trimethylsilyl enol ether 31 derived from naphthalenone 30. The
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