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Aliphatic and alicyclic building blocks

(-)-Irofulven

Also known as Irofulven, 6-Hydroxymethylacylfulvene, (hydroxymethyl)acylfulvene

CAS 158440-71-2Formula C15H18O3Molar mass 246.31 g/mol
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(-)-Irofulven chemical structure, C15H18O3, CAS 158440-71-2
2D chemical structure

Key facts

What buyers check first

All properties
CAS number
158440-71-2
Formula
C15H18O3
Molar mass
246.31 g/mol
HS code
291440
Category
Aliphatic and alicyclic building blocks

What is (-)-Irofulven?

Plain description, key identifiers and synonyms

Irofulven is a member of cyclohexenones.

Identifiers

Registry numbers, names and line notations, tap to copy

IUPAC name
(5'R)-5'-hydroxy-1'-(hydroxymethyl)-2',5',7'-trimethylspiro[cyclopropane-1,6'-indene]-4'-one
CAS number
158440-71-2 CAS number cross-checked
Molecular formula
C15H18O3
UNII
6B799IH05A
MDL number
MFCD00931906
InChIKey
NICJCIQSJJKZAH-AWEZNQCLSA-N
InChI
InChI=1S/C15H18O3/c1-8-6-10-12(11(8)7-16)9(2)15(4-5-15)14(3,18)13(10)17/h6,16,18H,4-5,7H2,1-3H3/t14-/m0/s1
Canonical SMILES
CC1=C(CO)C2=C(C)C3(CC3)C(C)(O)C(=O)C2=C1
Isomeric SMILES
CC1=C(C2=C(C3(CC3)[C@@](C(=O)C2=C1)(C)O)C)CO

Synonyms

  • Irofulven
  • 6-Hydroxymethylacylfulvene
  • (hydroxymethyl)acylfulvene
  • 6-(Hydroxymethyl)acylfulvene
  • Irofulvene
  • Irofulveno
  • HMAF cpd
  • irofulvenum
  • (6'R)-6'-hydroxy-3'-(hydroxymethyl)-2',4',6'-trimethyl-6',7'-dihydrospiro(cyclopropane-1,5'-indene)-7'-one
  • HMAF
  • MGI 114
  • (R)-Irofulven
  • (5'R)-5'-hydroxy-1'-(hydroxymethyl)-2',5',7'-trimethylspiro[cyclopropane-1,6'-indene]-4'-one
  • (6'R)-6'-Hydroxy-3'-(hydroxymethyl)-2',4',6'-trimethylspiro[cyclopropane-1,5'-[5H]inden]-7'(6'H)-one
  • (R)-6'-Hydroxy-3'-(hydroxymethyl)-2',4',6'-trimethylspiro(cyclopropane-1,5'-(5H)inden)-7'(6'H)-one
  • Spiro[cyclopropane-1,5'-[5H]inden]-7'(6'H)-one, 6'-hydroxy-3'-(hydroxymethyl)-2',4',6'-trimethyl-, (6'R)-
  • Acylfulvene, 6-(hydroxymethyl)-
  • (-)-(Hydroxymethyl)acylfulvene
  • Irofulven (USAN/INN)
  • (R)-6'-hydroxy-3'-(hydroxymethyl)-2',4',6'-trimethylspiro[cyclopropane-1,5'-inden]-7'(6'H)-one
  • Spiro(cyclopropane-1,5'(5H)-inden)-7'(6'H)-one, 6'-hydroxy-3'-(hydroxymethyl)-2',4',6'-trimethyl-, (R)-
  • (5'R)-5'-hydroxy-1'-(hydroxymethyl)-2',5',7'-trimethyl-spiro[cyclopropane-1,6'-indene]-4'-one
  • (6'R)-6'-hydroxy-3'-(hydroxymethyl)-2',4',6'-trimethylspiro[cyclopropane-1,5'-inden]-7'(6'H)-one

Physical and chemical properties

Measured values and descriptors computed from the structure

Physical and chemical properties

Measured values, check the supplier specification for your grade

No measured properties are recorded for this substance yet. Ask suppliers for a technical data sheet.

Values vary by grade. Ask suppliers for the COA or TDS of the batch you buy.

Computed descriptors

Calculated from the structure, useful for screening and formulation

Molecular weight
246.31 g/molcalc.
Exact mass
246.1256 Dacalc.
LogP (octanol/water)
1.67calc.
Topological polar surface area
57.53 Ųcalc.
Hydrogen bond donors
2calc.
Hydrogen bond acceptors
3calc.
Rotatable bonds
1calc.
Heavy atoms
18calc.
Rings
3calc.
Aromatic rings
0calc.
Fraction sp3 carbons
0.53calc.
Formal charge
0calc.
Stereocentres
1calc.
Lipinski rule of five
Passes (0 violations)calc.

Calculated for screening. Confirm critical figures with the supplier.

Murcko scaffold

The ring system that remains when every side chain is removed

Murcko scaffold of this chemical, O=C1CC2(C=C3C=CC=C13)CC2

O=C1CC2(C=C3C=CC=C13)CC2

3 rings, 12 atoms.

10 other chemicals share this scaffold

Safety and hazards

GHS classification summary, not a safety data sheet

No GHS hazard classification is recorded for this substance yet. That does not mean it is harmless.

GHS classification summary, not a safety data sheet (SDS). Classifications can differ by supplier, grade and concentration. Always check the supplier's SDS.

(-)-Irofulven suppliers

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All 2 suppliers

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2 suppliers in 1 country

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(-)-Irofulven price

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Uses and applications

What the substance is used for, by industry and function

Pharmacological actions

  • Antineoplastic Agents, Alkylating
  • Radiation-Sensitizing Agents

Roles

  • antineoplastic agent
  • pharmaceutical

Pharmacology

Irofulven is a semisynthetic sesquiterpene derivative of illudin S, a natural toxin isolated from the fungus Omphalotus illudens. Irofulven alkylates DNA and protein macromolecules, forms adducts, and arrests cells in the S-phase of the cell cycle. This agent requires NADPH-dependent metabolism by alkenal/one oxidoreductase for activity. Irofulven is more active in vitro against tumor cells of epithelial origin and is more resistant to deactivation by p53 loss and MDR1 than other alkylating agents. (NCI04)

Regulatory status

Inventories, regulations and trade controls that list this substance

No regulatory list memberships are recorded for this substance yet. Always check the rules of the importing and exporting country before trade.

HS code and trade data

Customs classification and reported world trade statistics

Global trade

World import and export statistics for the HS code (-)-Irofulven is traded under.

HS 2914.40Indicative HS code

Ketone-alcohols and ketone-aldehydes

World exports in 2024
$199M
+2.5% vs 2023, imports $247M
2019 to 2024
Top exporters
  1. China29.5%
  2. Germany14.4%
  3. Netherlands12.7%
Top importers
  1. United States37.2%
  2. Netherlands8.5%
  3. Germany6.4%
Reported customs values in USD, not prices.Full trade data

The HS code shown for (-)-Irofulven is indicative (it was assigned by structure rules). Confirm the classification with your customs broker before shipping.

Frequently asked questions

Quick answers about (-)-Irofulven, based on the data on this page

What is (-)-Irofulven?

Irofulven is a member of cyclohexenones.

Guides for buyers

Practical guides that help when you source, ship or handle (-)-Irofulven

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Data last updated 7 Oct 2026. Details may have changed, please confirm them with the supplier. Report an error on this page
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