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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

signalword

Warning

Hazard Classifications

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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
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
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
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
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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