Geraniol

Geraniol
Compound Structure:
Synonyms: (2E)-3,7-dimethylocta-2,6-dien-1-ol; Geranyl alcohol; trans-Geraniol; (E)-Geraniol; (E)-Nerol; beta-Geraniol; t-geraniol; 2,6-Octadien-1-ol, 3,7-dimethyl-, (2E)-; 3,7-Dimethyl-trans-2,6-octadien-1-ol; Guaniol; 2-trans-3,7-Dimethyl-2,6-octadien-1-ol; 3,7-D
Compound ID: NMPC-1072
PubChem ID:

637566

Molecular Formula: C10H18O
Canonical SMILES: CC(=CCCC(=CCO)C)C
InChIKey: GLZPCOQZEFWAFX-JXMROGBWSA-N
About the compound:

Geraniol is a monoterpenoid that comprises two prenyl units linked head-to-tail, featuring a hydroxy group at its tail end. It serves various roles including as a fragrance, an allergen, a volatile oil component, and a plant metabolite. Structurally, it is a primary alcohol and a 3,7-dimethylocta-2,6-dien-1-ol. Found in many essential oils of fruits, vegetables, and herbs, geraniol is present in rose oil, citronella, lemongrass, lavender, and other aromatic plants. It is emitted from the flowers of numerous plant species and is extensively used in the food, fragrance, and cosmetic industries. Geraniol exhibits a broad range of pharmacological activities, including antimicrobial, anti-inflammatory, antioxidant, anti-cancer, and neuroprotective properties. It has been shown to sensitize tumor cells to common chemotherapies and is considered a promising cancer chemopreventive agent. Geraniol is effective against various types of cancer, including breast, lung, colon, prostate, pancreatic, skin, liver, kidney, and oral cancers. Geraniol is recognized as generally-recognized-as-safe (GRAS) by both the Flavor and Extract Manufacturers Association (FEMA) and the Food and Drug Administration (FDA) of the United States. However, sensitivity to geraniol can be determined through clinical patch testing, as it can trigger increased histamine release and affect cell-mediated immunity. Geraniol is a natural product found in organisms like Xylopiasericea and Eupatorium cannabinum, among others. Known as beta-Geraniol, it is found in almonds and in free state or as esters in many essential oils, including geranium and palmarosa oil, where it is most abundantly present. It has a rose-like odor and is commonly used in perfumes, as well as flavorings for various fruits like peach, raspberry, grapefruit, and others. It is an isomer of nerol and belongs to the family of Monoterpenes.

GHS Hazard Statements

H317: May cause an allergic skin reaction [Warning Sensitization, Skin]

Properties:

Chemical and Physical Properties

Property Name

Property Value

Molecular Weight

154.25 g/mol

XLogP3-AA

2.9

Hydrogen Bond Donor Count

1

Hydrogen Bond Acceptor Count

1

Rotatable Bond Count

4

Exact Mass

154.135765193 g/mol

Monoisotopic Mass

154.135765193 g/mol

Topological Polar Surface Area

20.2Ų

Heavy Atom Count

11

Formal Charge

0

Complexity

150

Isotope Atom Count

0

Defined Atom Stereocenter Count

0

Undefined Atom Stereocenter Count

0

Defined Bond Stereocenter Count

1

Undefined Bond Stereocenter Count

0

Covalently-Bonded Unit Count

1

Compound Is Canonicalized

Yes

Physical Description

Geraniol is a colorless to pale yellow oily liquid with a sweet rose odor. (NTP, 1992)

Boiling Point

230 °C

Melting Point

-15 °C

Density

0.8894 g/cu cm at 20 °C

Solubility 

Insoluble in glycerol; slightly soluble in water; soluble in most fixed oils, propylene glycol

Vapor Pressure

0.03 [mmHg]

Source: PubChem

Source Species: Crateva adansonii
Garcinia kola
Monodora tenuifolia
Pachira glabra
Phyllanthus muellerianus
Cymbopogon citratus
Eremomastax speciosa
Napoleonaea imperialis
Hyparrhenia rufa
Plumeria alba
Pteris togoensis
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