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I7033

Sigma-Aldrich

6′-Iodoresiniferatoxin

amorphous semi-solid

Synonym(s):

6-I-RTX, Resiniferonyl 20-(4-hydroxy-2-iodo-5-methoxyphenylacetate 9,13,14-ortho(phenylacetate)

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About This Item

Empirical Formula (Hill Notation):
C37H39O9I
Molecular Weight:
754.60
MDL number:
MFCD09971005
UNSPSC Code:
12352200
PubChem Substance ID:
329815314
NACRES:
NA.77

form

amorphous semi-solid

Quality Level

100

color

colorless to white

storage temp.

−20°C

SMILES string

COc1cc(CC(=O)OCC2=CC3C4O[C@]6(Cc5ccccc5)O[C@]4(C[C@@H](C)[C@]3(O6)C7C=C(C)C(=O)[C@@]7(O)C2)C(C)=C)c(I)cc1O

InChI

1S/C37H39IO9/c1-20(2)35-16-22(4)37-26(33(35)45-36(46-35,47-37)18-23-9-7-6-8-10-23)12-24(17-34(42)30(37)11-21(3)32(34)41)19-44-31(40)14-25-13-29(43-5)28(39)15-27(25)38/h6-13,15,22,26,30,33,39,42H,1,14,16-19H2,2-5H3/t22-,26?,30-,33-,34-,35-,36-,37-/m1/s1

InChI key

IITCVPTZKLXSKQ-DCLOTLOASA-N

Biochem/physiol Actions

VR1 vanilloid receptor partial agonist.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

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Mark E McDonnell et al.
Bioorganic & medicinal chemistry letters, 12(8), 1189-1192 (2002-04-06)
Using a 'directed' iodination procedure, novel iodo-resiniferatoxin congeners were synthesized from 4-acetoxy-3-methoxyphenylacetic acid and resiniferinol- 9,13,14-ortho-phenylacetate (ROPA). The 2-iodo-4-hydroxy-5-methoxyphenylacetic acid ester of resiniferinol 5 displayed high affinity binding (K(i)=0.71 nM) for the human vanilloid VR1 receptor and functioned as a

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