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Terpenes Floral Citronellol
Floral

Citronellol

Citronellol is the rosy, waxy, slightly leathery terpene alcohol of rose, geranium, and citronella oils. Its (−) form is rose and geranium; its (+) form is citronella. Rat studies show blood-pressure lowering and analgesic signals; oxidized citronellol is an EU-labelled fragrance allergen.

Aroma

Floral, Rose, Citrus, Sweet

Sensory Descriptors

rosefloralwaxycitrusleathergreengeraniumcitronella

Boiling Point

225°C (437°F)

Found In

Rose, Geranium, Citronella Grass, Lemongrass

Effects

Anti-inflammatory, Anti-microbial, Insect Repellent, Anti-spasmodic

Industries

FragranceCulinaryAromatherapyCosmetics

Aroma and sensory profile

Citronellol is rose with the sweetness turned down and the wax turned up. Fragrance references type it floral with medium strength and describe it neat as floral, leather, waxy, rose bud, and citrus, or floral, rosy, and sweet citrus with green, fatty terpene nuances; its flavor at 20 parts per million is floral, rose, sweet, and green with fruity citrus nuances [1]. Against geraniol, the other rose alcohol, citronellol is fresher, waxier, and more petal than perfume, with a faint leathery or fatty edge that geraniol lacks.

The molecule, 3,7-dimethyloct-6-en-1-ol, has one stereocenter and is chiral. (−)-citronellol, the form of rose and geranium oils, is described as floral, rose, waxy, geranium oil, and powdery, with a substantivity of 56 hours on a blotter [2]. (+)-citronellol, the form of citronella oils, is described as citronella oil, rose, leaf, oily, and petal [3]. The (−) form is the finer rose; the (+) form is greener and more citronella. HSDB records that citronellol occurs in both enantiomeric forms, with rose and geranium the richest sources [4].

Effects and research

No human trial of citronellol was found. A 2019 systematic review of 32 papers found antibiotic and antifungal activity in vitro and analgesic and anticonvulsant activity in vivo, called it a promising molecule for future pharmacological study, and acknowledged the absence of human evidence [5]. The Research Institute for Fragrance Materials assessed the racemate in 2023 [8].

The cardiovascular result is the most specific. In rats, intravenous citronellol at 1 to 20 milligrams per kilogram produced dose-dependent hypotension and tachycardia, and in isolated mesenteric artery rings it relaxed contractions fully and antagonized calcium-induced contraction by 97 percent, a direct vascular smooth muscle effect [6]. In mice, intraperitoneal citronellol at 25 to 100 milligrams per kilogram reduced mechanical hyperalgesia induced by carrageenan, tumor necrosis factor alpha, prostaglandin E2, and dopamine, with reduced activation of spinal cord lamina I [7].

One inhalation result cuts against the aromatherapy reputation. Mice exposed to beta-citronellol vapor for 30 minutes showed increased anxiety-like behavior in the elevated plus maze and open field, with no change in memory or depression tests and no attraction or aversion to the odor itself; the authors advised caution with essential oils and cosmetics containing it [9]. It is one study, but it is the only inhalation behavioral study of citronellol found, and it did not find calm.

Natural sources

Citronellol is a rose, geranium, and citronella terpene. HSDB records it as widespread in nature in both enantiomeric forms, occurring in about 70 essential oils, with rose and geranium the richest sources [4], and the 2019 review adds the Cymbopogon grasses and Citrus species used in cooking and traditional medicine [5]. Fragrance databases note its isolation from geranium oil and lemon eucalyptus [1], place the (−) form in geranium oil, nutmeg, orange, apple juice, beer, bilberry, and black currant [2], and the (+) form in black cumin seed and across the citrus family [3]. In cannabis citronellol is a trace terpenoid, occasionally reported in floral chemotypes and more often absent.

Boiling point and vaporization

PubChem compiles citronellol's boiling point as 225 °C from the Joint FAO/WHO Expert Committee on Food Additives and 224 °C from the CRC Handbook, with the Merck Index giving 108 to 109 °C at 10 mmHg for the (−) form [4]; fragrance references list 225 °C at 760 mmHg and 105 °C at 15 mmHg [1]. This profile keeps 225 °C (437 °F), the JECFA value, which matches what the site already listed. That places citronellol just below geraniol in the heart-note band, and its 56-hour blotter substantivity [2] shows how slowly it leaves a surface. Its instability is oxidative: on air exposure it autoxidizes to hydroperoxides that are the main skin sensitizers in the aged material [10]. No thermal degradation study of citronellol was found.

Safety and regulation

Citronellol is listed by the US Food and Drug Administration as a permitted synthetic flavoring substance at 21 CFR 172.515, as "Citronellol; 3,7-dimethyl-6-octen-1-ol; d-citronellol" [12]. The Research Institute for Fragrance Materials assessed dl-citronellol in 2023 [8]. No cancer classification applies.

Its skin record follows the pattern of geraniol and linalool. Pure citronellol is a weak sensitizer; air-exposed citronellol loses concentration and gains potency, and hydroperoxides are its major oxidation products and main skin sensitizers [10]. In a series of 658 dermatitis patients, purified citronellol gave positive patch tests in 0.15 to 0.31 percent, oxidized citronellol in 0.61 to 4.5 percent [11]. Under Europe's classification inventory, 99.6 percent of notifications flag it as a skin sensitizer, 96 percent as a skin irritant, and 65 percent as a serious eye irritant [4], and it is among the fragrance allergens that must be declared on European cosmetic labels above threshold.

Industries and uses

Fragrance: citronellol is a foundation rose material in floral, rose, and geranium accords and one of the highest-volume fragrance alcohols, stocked as racemic and single-enantiomer grades [1][2][3]. Culinary: it holds FDA flavoring status and contributes rosy, green, fruity-citrus nuances at low parts-per-million levels [1][12]. Aromatherapy: rose, geranium, and citronella oils are its carriers; the oxidation and patch-test data, and the mouse anxiety result, are the relevant cautions [9][11]. Cosmetics: it is a declarable fragrance allergen in Europe, so formulators track its level and oxidation state [4][11].

References

  1. citronellol, CAS 106-22-9. The Good Scents Company
  2. laevo-citronellol, (-)-3,7-dimethyl-6-octen-1-ol. The Good Scents Company
  3. (R)-(+)-beta-citronellol, CAS 1117-61-9. The Good Scents Company
  4. Citronellol, CID 8842: boiling point (JECFA, CRC, Merck), natural occurring sources (HSDB), GHS classification. PubChem, National Library of Medicine
  5. Citronellol, a monoterpene alcohol with promising pharmacological activities: A systematic review. Food and Chemical Toxicology (2019)
  6. Hypotensive and vasorelaxant effects of citronellol, a monoterpene alcohol, in rats. Basic & Clinical Pharmacology & Toxicology (2010)
  7. Citronellol, a natural acyclic monoterpene, attenuates mechanical hyperalgesia response in mice: Evidence of the spinal cord lamina I inhibition. Chemico-Biological Interactions (2015)
  8. RIFM fragrance ingredient safety assessment, dl-citronellol, CAS Registry Number 106-22-9. Food and Chemical Toxicology (2023)
  9. Increased anxiety-related behavior in mice following β-citronellol inhalation. Libyan Journal of Medicine (2020)
  10. Characterization of skin sensitizers from autoxidized citronellol: impact of the terpene structure on the autoxidation process. Contact Dermatitis (2014)
  11. Patch testing with purified and oxidized citronellol. Contact Dermatitis (2020)
  12. 21 CFR 172.515, Synthetic flavoring substances and adjuvants. Code of Federal Regulations (Legal Information Institute)

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