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Heterocyclic compounds

Helenalin

Also known as Helenalin A, PF 56, 6alpha,8beta-Dihydroxy-4-oxoambrosa-2,11(13)-dien-12-oic acid 12,8-lactone

CAS 6754-13-8Formula C15H18O4Molar mass 262.31 g/molEC 111-092-8
GHS signal word: Danger. Pictograms: Acute toxicity (severe) 5 suppliers listed
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Helenalin chemical structure, C15H18O4, CAS 6754-13-8
2D chemical structure

Key facts

What buyers check first

All properties
Appearance
Sternutative crystals from benzene
Melting point
167 to 168
Solubility
SLIGHTLY SOL IN WATER, SOL IN ALCOHOL, CHLOROFORM, HOT BENZENE
HS code
293220
Category
Heterocyclic compounds
Illustrative photo, drums, an IBC tote and sacks in a chemical warehouse in a warehouse
Typical packagingIllustrative packaging image, not the actual product

What is Helenalin?

Plain description, key identifiers and synonyms

Helenalin is a sesquiterpene lactone that is 3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione substituted by a hydroxy group at position 4, methyl groups at positions 4a and 8 and a methylidene group at position 3 (the 3aS,4S,4aR,7aR,8R,9aR stereoisomer). It has a role as a metabolite, an antineoplastic agent, an anti-inflammatory agent and a plant metabolite. It is an organic heterotricyclic compound, a secondary alcohol, a gamma-lactone, a sesquiterpene lactone and a cyclic ketone.

Identifiers

Registry numbers, names and line notations, tap to copy

IUPAC name
(3aR,5R,5aR,8aR,9S,9aS)-9-hydroxy-5,8a-dimethyl-1-methylidene-3a,4,5,5a,9,9a-hexahydroazuleno[6,7-b]furan-2,8-dione
CAS number
6754-13-8 CAS number cross-checked
EC number
111-092-8
Molecular formula
C15H18O4
UNII
4GUY9L896T
MDL number
MFCD01674580
InChIKey
ZVLOPMNVFLSSAA-XEPQRQSNSA-N
InChI
InChI=1S/C15H18O4/c1-7-6-10-12(8(2)14(18)19-10)13(17)15(3)9(7)4-5-11(15)16/h4-5,7,9-10,12-13,17H,2,6H2,1,3H3/t7-,9+,10-,12-,13+,15+/m1/s1
Canonical SMILES
C=C1C(=O)OC2CC(C)C3C=CC(=O)C3(C)C(O)C12
Isomeric SMILES
C[C@@H]1C[C@@H]2[C@H]([C@@H]([C@]3([C@H]1C=CC3=O)C)O)C(=C)C(=O)O2

Synonyms

  • Helenalin A
  • PF 56
  • 6alpha,8beta-Dihydroxy-4-oxoambrosa-2,11(13)-dien-12-oic acid 12,8-lactone
  • (3aR,5R,5aR,8aR,9S,9aS)-9-hydroxy-5,8a-dimethyl-1-methylidene-3a,4,5,5a,9,9a-hexahydroazuleno[6,7-b]furan-2,8-dione
  • Ambrosa-2,11(13)-dien-12-oic acid, 6alpha,8beta-dihydroxy-4-oxo-, 12,8-lactone
  • (3aR,5R,5aR,8aR,9S,9aS)-9-hydroxy-5,8a-dimethyl-1-methylene-3a,4,5,5a,9,9a-hexahydroazuleno[6,7-b]furan-2,8-dione
  • Azuleno(6,5-b)furan-2,5-dione, 3,3a,4,4a,7a,8,9,9a-octahydro-4-hydroxy-4a,8-dimethyl-3-methylene-, (3aS-(3aalpha,4alpha,4abeta,7aalpha,8alpha,9aalpha))-
  • (3aR,5R,5aR,8aR,9S,9aS)-9-hydroxy-5,8a-dimethyl-1-methylene-3a,4,5,5a,9,9a-hexahydroazuleno(6,7-b)furan-2,8-dione
  • (3aR,5R,5aR,8aR,9S,9aS)-9-hydroxy-5,8a-dimethyl-1-methylidene-3a,4,5,5a,9,9a-hexahydroazuleno(6,7-b)furan-2,8-dione
  • Ambrosa-2,11(13)-dien-12-oic acid, 6-alpha,8-beta-dihydroxy-4-oxo-, 12,8-lactone
  • (3aR,5R,5aR,8aR,9S,9aS)-9-Hydroxy-5,8a-dimethyl-1-methylidene-3a,4,5,5a,9,9a-hexahydroazuleno[7,6-d]furan-2,8-dione
  • (3aS,4S,4aR,7aR,8R,9aR)-4-hydroxy-4a,8-dimethyl-3-methylene-3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione
  • (3aS,4S,4aR,7aR,8R,9aR)-4-hydroxy-4a,8-dimethyl-3-methylidene-3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione
  • (-)-Helenalin
  • (3aS)-3,3aalpha,4alpha,4a,7aalpha,8,9,9aalpha-Octahydro-4-hydroxy-4abeta,8 alpha-dimethyl-3-methyleneazuleno(6,5-b)-furan-2,5-dione
  • 4-18-00-01434 (Beilstein Handbook Reference)
  • Natural sesquiterpenoid from Arnica species
  • Ambrosa-2, 6alpha,8beta-dihydroxy-4-oxo-, 12,8-lactone
  • (3aR,5R,5aR,8aR,9S,9aS)-5,8a-dimethyl-1-methylidene-9-oxidanyl-3a,4,5,5a,9,9a-hexahydroazuleno[6,7-b]furan-2,8-dione
  • (3aR,5R,5aR,8aR,9S,9aS)-9-hydroxy-5,8a-dimethyl-1-methylene-3a,4,5,5a,9,9a-hexahydroazuleno[6,7-b]furan-2,8-quinone
  • (3aS)-3,3aalpha,4alpha,4a,7aalpha,8,9,9aalpha-octahydro-4-hydroxy-4abeta,8alpha-dimethyl-3-methyleneazuleno(6,5-b)-furan-2,5-dione
  • (3As-(3a.alpha.,4alpha,4a.beta.,7a.alpha.,8alpha,9a.alpha.))-3,3a,4,4a,7a,8,9,9a-octahydro-4-hydroxy-4a,8-dimethyl-3-methyleneazuleno(6,5-b)furan-2,5-dione
  • 4-Hydroxy-4a,8-dimethyl-3-methylene-3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione
  • Azuleno[6,5-dione, 3,3a,4,4a,7a,8,9,9a-octahydro-4-hydroxy-4a,8-dimethyl-3-methylene-, [3aS-(3aalpha,4alpha,4abeta,7aalpha,8alpha,9aalpha)]-

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

Appearance
Sternutative crystals from benzeneexp.
Taste
BITTERexp.
Melting point
167 to 168exp.
Solubility
SLIGHTLY SOL IN WATER, SOL IN ALCOHOL, CHLOROFORM, HOT BENZENEexp.

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
262.31 g/molcalc.
Exact mass
262.1205 Dacalc.
LogP (octanol/water)
1.25calc.
Topological polar surface area
63.6 Ųcalc.
Hydrogen bond donors
1calc.
Hydrogen bond acceptors
4calc.
Rotatable bonds
0calc.
Heavy atoms
19calc.
Rings
3calc.
Aromatic rings
0calc.
Fraction sp3 carbons
0.6calc.
Formal charge
0calc.
Stereocentres
6calc.
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, C=C1C(=O)OC2CCC3C=CC(=O)C3CC12

C=C1C(=O)OC2CCC3C=CC(=O)C3CC12

3 rings, 16 atoms.

22 other chemicals share this scaffold

Safety and hazards

GHS classification summary, not a safety data sheet

GHS signal word
Danger
GHS06: Acute toxicity (severe)
Acute toxicity (severe)

Hazard statements

  • H301Toxic if swallowed.
Precautionary statements (7)
  • P264Wash skin thoroughly after handling.
  • P270Do not eat, drink or smoke when using this product.
  • P301 + P316If swallowed: Get emergency medical help immediately.
  • P321Specific treatment (see supplemental first aid instructions on the label).
  • P330Rinse mouth.
  • P405Store locked up.
  • P501Dispose of contents and container in accordance with local regulations.

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

Full safety data and first aid

Helenalin suppliers

Sponsored listings first, then the documented ranking: membership, verification, replies, completeness, freshness and ratings

All 5 suppliers
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Where suppliers are based

5 suppliers in 3 countries

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Helenalin price

Indicative price range per kg from live supplier offers

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Uses and applications

What the substance is used for, by industry and function

Pharmacological actions

  • Anti-Inflammatory Agents, Non-Steroidal
  • Antineoplastic Agents, Phytogenic
  • Cardiotonic Agents
  • Platelet Aggregation Inhibitors

Roles

  • anti-inflammatory agent
  • antineoplastic agent
  • eukaryotic metabolite
  • metabolite
  • pharmaceutical
  • plant metabolite

How it is made

Pseudoguaianolide sesquiterpenoid lactone from helenium autumnale l, h amarum (raf) h roch, h microcephalum dc, compositae. Isolation: clark, j am chem soc 58, 1982 (1936), adams, horz, j am chem soc 71, 2546 (1949).

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 Helenalin is traded under.

HS 2932.20Indicative HS code

Lactones

World exports in 2024
$1.97B
−4.7% vs 2023, imports $2.07B
2019 to 2024
Top exporters
  1. China56.3%
  2. India * partner reported7.4%
  3. Germany7.3%
Top importers
  1. United States14.2%
  2. India * partner reported13.5%
  3. Brazil8.5%

* Partner reported figures, a lower bound.

Reported customs values in USD, not prices.Full trade data

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

Frequently asked questions

Quick answers about Helenalin, based on the data on this page

What is Helenalin?

Helenalin is a sesquiterpene lactone that is 3,3a,4,4a,7a,8,9,9a-octahydroazuleno[6,5-b]furan-2,5-dione substituted by a hydroxy group at position 4, methyl groups at positions 4a and 8 and a methylidene group at position 3 (the 3aS,4S,4aR,7aR,8R,9aR stereoisomer).

What is the CAS number of Helenalin?

The CAS registry number of Helenalin is 6754-13-8.

What is the molecular formula and weight of Helenalin?

The molecular formula of Helenalin is C15H18O4 and its molar mass is 262.31 g/mol.

What is Helenalin used for?

Known uses and roles of Helenalin include anti-inflammatory agent, antineoplastic agent, eukaryotic metabolite, metabolite, pharmaceutical and 5 more.

Is Helenalin hazardous?

Helenalin carries the GHS signal word "Danger". Main hazards: toxic if swallowed. This summary is not an SDS, always read the supplier safety data sheet.

What is the HS code of Helenalin?

Helenalin is usually classified under HS code 293220 (Lactones). This is indicative, confirm it with your customs broker before shipping.

Where can I buy Helenalin?

CompoundList lists 5 suppliers of Helenalin in China, United Kingdom and United States. Send one free request to get and compare quotes. Your contact details stay private until you accept a quote.

What is the price of Helenalin?

Suppliers quote Helenalin on request because prices depend on grade, purity, quantity and destination. A free request on CompoundList gets you several quotes to compare.

Guides for buyers

Practical guides that help when you source, ship or handle Helenalin

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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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