3,3'-Diindolylmethane

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3,3'-Diindolylmethane
3,3'-Diindolylmethane.svg
Names
Preferred IUPAC name
3,3′-Methylenedi(1H-indole)
Other names
3-(1H-Indol-3-ylmethyl)-1H-indole
3,3′-Methylenebis-1H-indole
DIM
Identifiers
3D model (JSmol)
223072
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.124.716 Edit this at Wikidata
EC Number
  • 606-355-3
UNII
  • InChI=1S/C17H14N2/c1-3-7-16-14(5-1)12(10-18-16)9-13-11-19-17-8-4-2-6-15(13)17/h1-8,10-11,18-19H,9H2 checkY
    Key: VFTRKSBEFQDZKX-UHFFFAOYSA-N checkY
  • InChI=1/C17H14N2/c1-3-7-16-14(5-1)12(10-18-16)9-13-11-19-17-8-4-2-6-15(13)17/h1-8,10-11,18-19H,9H2
  • InChI=1/C17H14N2/c1-3-7-16-14(5-1)12(10-18-16)9-13-11-19-17-8-4-2-6-15(13)17/h1-8,10-11,18-19H,9H2
    Key: VFTRKSBEFQDZKX-UHFFFAOYAU
  • c4ccc3c(Cc1c[nH]c2ccccc12)c[nH]c3c4
Properties
C17H14N2
Molar mass 246.313 g·mol−1
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H315, H319, H335, H413
P261, P264, P271, P273, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
☒N verify (what is checkY☒N ?)

3,3′-Diindolylmethane (DIM) is a compound derived from the digestion of indole-3-carbinol, found in cruciferous vegetables, such as broccoli, Brussels sprouts, cabbage and kale.[1] It and its parent compound – indole-3-carbinol – are under laboratory research to determine their possible biological properties, particularly in anti-cancer mechanisms.[1][2][3] DIM is sold as a dietary supplement.[1]

Properties[edit]

In vitro, DIM has action as a histone deacetylase inhibitor,[1] specifically against HDAC1, HDAC2, and HDAC3.[4] DIM is a metabolite of indole-3-carbinol.[1][2][3]

See also[edit]

References[edit]

  1. ^ a b c d e "Indole-3-carbinol". Micronutrient Information Center, Linus Pauling Institute, Oregon State University. 1 July 2017. Retrieved 11 July 2022.
  2. ^ a b "Indole-3-Carbinol". Memorial Sloan Kettering Cancer Center. Retrieved 2019-09-03.
  3. ^ a b "3,3'-Diindolylmethane". PubChem, US National Library of Medicine. 9 July 2022. Retrieved 11 July 2022.
  4. ^ Rajendran, P; Ho, E; Williams, DE; Dashwood, RH (2011). "Dietary phytochemicals, HDAC inhibition, and DNA damage/repair defects in cancer cells". Clin Epigenetics. 3 (1): 4. doi:10.1186/1868-7083-3-4. PMC 3255482. PMID 22247744.

External links[edit]