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Geosmin

Athanor · official

C12H22O · 182.3 g/mol

IUPAC name: (4S,4aS,8aR)-4,8a-dimethyl-1,2,3,4,5,6,7,8-octahydronaphthalen-4a-ol

Also called petrichor, earthy smell

Natural products
Open in Athanor
The structure of Geosmin
Drawn from its SMILES with RDKit
Harmful or irritantWarningHarmful if swallowed

Names and identifiers

IUPAC name
(4S,4aS,8aR)-4,8a-dimethyl-1,2,3,4,5,6,7,8-octahydronaphthalen-4a-ol
Synonyms
petrichor, earthy smell, (-)-geosmin
+ 37 more

MYW912WXJ4, Octahydro-4alpha,8abeta-dimethyl-4aalpha(2H)-naphthol, trans-1,10-Dimethyl-trans-9-decalol, (4S,4aS,8aR)-4,8a-dimethyloctahydronaphthalen-4a(2H)-ol, (4S,4aS,8aR)-4,8a-dimethyl-1,2,3,4,5,6,7,8-octahydronaphthalen-4a-ol, FEMA NO. 4682, CHEBI:46702, DTXSID801024112, RefChem:142945, CHEBI:46703, DTXCID001508382, 243-239-8, trans-1,10-dimethyl-trans-decalol, (4S-(4alpha,4aalpha,8abeta))-Octahydro-4,8a-dimethyl-4a(2H)-naphthol, (4S,4aS,8aR)-4,8a-dimethyl-decahydronaphthalen-4a-ol, 4a(2H)-Naphthalenol, octahydro-4,8a-dimethyl-, [4S-(4.alpha.,4a.alpha.,8a.beta.)]-, 4a(2H)-Naphthalenol, octahydro-4,8a-dimethyl-,(4.alpha.,4a.alpha.,8a.beta.)-, 1,10-Dimethyl-9-decalol, EINECS 243-239-8, UNII-MYW912WXJ4, rac Geosmin, 4,8a-Dimethyloctahydro-4a(2H)-naphthalenol #, 4,8alpha-dimethyl-octahydro-naphthalen-4alpha-ol, GEOSMIN [MI], 39 - Geosmin and MIB, SCHEMBL50009, 4a-.alpha.-(2H)-Naphthol, octahydro-4-.alpha.,8a-.beta.-dimethyl-, CHEMBL2374043, (4S,4aS,8aR)-Octahydro-4,8a-dimethyl-4a(2H)-naphthalenol, 4a-alpha-(2H)-Naphthol, octahydro-4-alpha,8a-beta-dimethyl-, MSK005063-100M, 4a(2H)-Naphthalenol, octahydro-4,8a-dimethyl-, (4S-(4-alpha,4a-alpha,8a-beta))-, Geosmin Solution in Methanol, 100ug/mL, MSK005063-1000M, NCGC00165950-01, (+/-)-Geosmin 10 microg/mL in Methanol, Geosmin Solution in Methanol, 1000ug/mL

Molecular formula
C12H22O
Empirical formula
C12H22O
Molecular weight
182.3 g/mol
Exact mass
182.16707
CAS number
19700-21-1
PubChem CID
29746
Canonical SMILES
CC1CCCC2(C1(CCCC2)O)C
Isomeric SMILES
C[C@H]1CCC[C@@]2([C@@]1(CCCC2)O)C
InChI
InChI=1S/C12H22O/c1-10-6-5-8-11(2)7-3-4-9-12(10,11)13/h10,13H,3-9H2,1-2H3/t10-,11+,12-/m0/s1
InChIKey
JLPUXFOGCDVKGO-TUAOUCFPSA-N
Molfile

Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.

Calculated

Heavy atoms
13
Rings
2
Aromatic rings
0
Fraction sp³ carbons (Fsp3)
1
H-bond donors
1
H-bond acceptors
1
Rotatable bonds
0
TPSA (Ų)
20.2
Formal charge
0
XLogP3
3.3 PubChem
Complexity
201 PubChem
Stereocenters
3 defined, 1 undefinedCIP: C2: R · C6: R · C8: S · C12: undefined
Double-bond geometry
None specified
Point group
C1 of one 3D conformer with its hydrogens, by Athanor’s engine (as in the app)

Elemental analysis

  • C79.06%
  • H12.16%
  • O8.78%

Isotope pattern

100%182.16713%183.1711.0%184.173

Each peak is a nominal mass with its abundance-weighted exact mass, as a percentage of the tallest, from IUPAC natural isotope abundances.

Computed from the structure with RDKit 2026.09 when this page was built, beside PubChem's own computed values from its record; where the two differ, both are shown.

Predicted

log P
2.97 Crippen (Wildman and Crippen 1999)
log S (water solubility)
-2.84 ESOL (Delaney 2004), log mol/L
Synthetic accessibility
3.49 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)

Drug-likeness: Lipinski’s rule of five

  • Molecular weight ≤ 500: 182.31
  • log P ≤ 5 (Crippen): 2.97
  • H-bond donors ≤ 5: 1
  • H-bond acceptors ≤ 10: 1

Passes all four rules.

¹³C NMR shifts, predicted

Predictions, not measurements; each names its method. A measured log P, where a source reports one, is under Physical properties.

Safety

Warning

Most widely reported: 89 company reports to ECHA. Source [1].

  • Harmful or irritant
  • H302Harmful if swallowed

Precautionary statements: P264, P270, P301+P317, P330, P501

Safety data sheets on the supplier’s page: LGC Standards, BenchChem, A2B Chem.

Always read the supplier’s safety data sheet before working with it.

Spectra

Experimental spectra held by these sources; each link opens the source's own record.

Literature

Reading PubChem, OpenAlex and GSRS…

Bioactivity

Reading ChEMBL…

References

  1. [1]European Chemicals Agency (ECHA) · ECHA legal notice: reuse with acknowledgement · via PubChem · retrieved 2026-10-14
  2. [2]SpectraBase · Linked only · via PubChem · retrieved 2026-10-14
  3. ·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
  4. ·Literature on PubChem

Data last updated 2026-10-14.