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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

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Certificates of Analysis (COA)

Lot/Batch Number
090K4701

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M Jonassohn et al.
Bioorganic & medicinal chemistry, 5(7), 1363-1367 (1997-07-01)
The resolution of synthetic (+/-)-isovelleral (1), via chromatographic separation of the two diastereomers of the (-)-menthoxyacetic acid diester of the corresponding (+/-)-diol (3), yielded both enantiomers of the bioactive fungal metabolite (+)-isovelleral (1). While the antimicrobial and cytotoxic activities of
A Szallasi et al.
British journal of pharmacology, 119(2), 283-290 (1996-09-01)
1. The irritant fungal terpenoid isovelleral caused protective eye-wiping movements in the rat upon intraocular instillation and showed cross-tachyphylaxis with capsaicin, the pungent principle in hot pepper. 2. Isovelleral induced a dose-dependent calcium uptake by rat dorsal root ganglion neurones
A Forsby et al.
Natural toxins, 2(2), 89-95 (1994-01-01)
The effect of the three sesquiterpenoid unsaturated dialdehydes--polygodial, isovelleral, and epipolygodial--on intracellular free Ca2+ concentration, [Ca2+]i, was investigated in the human neuroblastoma cell line SH-SY5Y. [Ca2+]i was measured by the Fura-2 spectrophotofluorometric technique in multi-cell and single-cell experiments. Polygodial and
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
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
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