Overview

Estratetraenol (estra-1,3,5(10),16-tetraen-3-ol) is a putative female pheromone found in female sweat and pregnant woman's urine. It's structurally related to estrogens but has NO estrogenic activity due to the C16=C17 double bond replacing the 17ฮฒ-hydroxyl group.

The community is divided on its usefulness, with some viewing it as a comfort enhancer and others arguing it signals "pregnancy" and kills sexual attraction.

Pharmacology

What It Is

Estratetraenol (estra-1,3,5(10),16-tetraen-3-ol) is a C18 estratetraene steroid โ€” an estrane skeleton with four double bonds (at C1-C2, C3-C4, C5-C10, and C16-C17), plus a 3-hydroxyl (phenolic OH). Molecular formula Cโ‚โ‚ˆHโ‚‚โ‚‚O, MW 254.37. Despite being structurally related to estrogens, it has NO estrogenic activity โ€” the C16=C17 double bond replaces the 17ฮฒ-hydroxyl group that is essential for estrogen receptor binding.

Biosynthesis

Estratetraenol is found in female sweat and pregnant women's urine, consistent with its characterization as a putative female pheromone. Its biosynthetic pathway is not fully elucidated but it is derived from the estrane/estrogen pathway:

Cholesterol โ†’ Pregnenolone โ†’ DHEA โ†’ Androstenedione โ†’ Estrone โ†’ Estratetraenol
                                                                  (via 16-dehydration)

Detection & Chemistry

Detected via VNO (close-range, non-volatile). The 16-position double bond is chemically critical:

  • Replaces the 17ฮฒ-OH required for estrogen receptor binding โ†’ non-estrogenic
  • Any compound marketed as "estratetraenone" with a 16-double bond is chemically impossible โ€” the C17 ketone position is occupied by the double bond
  • The aromatic A-ring (phenol) provides some polarity, limiting volatility

Detection Pathway

Estratetraenol is non-volatile (no vapor pressure data available, estimated very low). Detection is likely through:

  • VNO pumping mechanism: Mucus transport of non-volatile compounds
  • Direct contact: Close-proximity interactions

This explains why effects are primarily seen in intimate/close settings rather than diffusively.

Related Compounds

Compound CAS Difference
Methoxyestratetraenol (MEO-EST) 28336-31-4 Methyl ether - more potent, non-prodrug
Estratetraenol acetate Unknown Acetate ester - prodrug form
8,9-Dehydroestrone 474-87-3 DIFFERENT - horse estrogen, IS estrogenic

Important Warnings

Mislabeling Issues

Many vendors sell "estratetraenone" which is chemically problematic:

  • The 16-position double bond precludes a 17-ketone
  • May actually be 8,9-dehydroestrone (horse estrogen, IS estrogenic)
  • Or mislabeled methoxyestratetraenol
  • Always verify CAS numbers

Not for HRT

Despite the name similarity to estrogens, estratetraenol has zero estrogenic activity and is not suitable for hormone replacement.