Etymology
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pip (n.1)

1797, "seed of an apple (or orange)," a shortened form of pipin "seed of a fleshy fruit" (early 14c.), from Old French pepin (13c.), probably from a root *pipp-, expressing smallness (compare Italian pippolo, Spanish pepita "seed, kernel").

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pip (n.2)

"disease of poultry consisting of a secretion of thick mucus which forms a white scale around the tongue," late 14c., pippe, probably from Middle Dutch pippe "mucus," from West Germanic *pipit (source also of East Frisian pip, Middle High German pfipfiz, German Pips), an early borrowing from Vulgar Latin *pippita, an unexplained alteration of Latin pituita "phlegm" (see pituitary).

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pip (n.3)

"one of the spots on a playing card, dice, etc.," c. 1600, peep, of unknown origin. Because of the original form and difference of dates, it is now not considered to be from pip (n.1). Related: Pips.

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pippin (n.)

"excellent person or thing," 1897, a sense extended from coveted varieties of apple that were raised from seed (so called since late 14c.), from Middle English pipin "seed of certain fruits" (see pip (n.1)).

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pip-pip 
slangy salutation current in Britain c. 1907-1923, said by Partridge to be in imitation of bicycle horn noise.
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pipsqueak (n.)

also pip-squeak, contemptuous name for an insignificant person, 1910, from the trivial noise a young or weak creature makes. In World War I it was the soldier's slang name for a small German shell "which makes both a pip and a squeak when it comes over the trenches" [Farrow, "Dictionary of Military Terms," 1918]. Pip and Squeak (and later Wilfred), the beloved English comic strip animals, debuted May 1919 in the children's section of the Daily Mirror. To squeeze (something) until the pips squeak "exact the maximum from" is attested by 1918, from pip (n.1).  

The grossest spectacle was provided by Sir Eric Geddes in the Guildhall at Cambridge. An earlier speech in which, in a moment of injudicious candour, he had cast doubts on the possibility of extracting from Germany the whole cost of the war had been the object of serious suspicion, and he had therefore a reputation to regain. "We will get out of her all you can squeeze out of a lemon and a bit more," the penitent shouted, "I will squeeze her until you can hear the pips squeak" ; his policy was to take every bit of property belonging to Germans in neutral and Allied countries, and all her gold and silver and her jewels, and the contents of her picture-galleries and libraries, to sell the proceeds for the Allies' benefit. [John Maynard Keynes, "The Economic Consequences of Peace," 1919]
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apple-seed (n.)

"the pip of an apple," 1690s, from apple + seed (n.).

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kernel (n.)
"edible substance in a nut or the stone of a fruit," Old English cyrnel "seed, kernel, pip," from Proto-Germanic *kurnilo- (source also of Middle High German kornel "a grain," Middle Dutch cornel "coarse meal"), from the root of corn "seed, grain" (from PIE root *gre-no- "grain") + -el, diminutive suffix. Figurative sense of "core or central part of anything" is from 1550s.
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Emma 
fem. proper name, from German Emma, from Erma, contraction of Ermentrude or some similar name. With lower-case -e-, as British telephone and radio enunciation of -m- (to avoid confusion with -n-), attested by 1891, common in British soldier's jargon in World War I, for example ack emma "a.m.," pip emma "p.m." Compare ack (-a-), toc (-t-).
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grain (n.)
early 14c., "a small, hard seed," especially of one of the cereal plants, also as a collective singular, "seed of wheat and allied grasses used as food;" also "something resembling grain; a hard particle of other substances" (salt, sand, later gunpowder, etc.), from Old French grain, grein (12c.) "seed, grain; particle, drop; berry; grain as a unit of weight," from Latin granum "seed, a grain, small kernel," from PIE root *gre-no- "grain." From late 14c. as "a species of cereal plant." In the U.S., where corn has a specialized sense, it is the general word (used of wheat, rye, oats, barley, etc.).

Figuratively, "the smallest possible quantity," from late 14c. From early 15c. in English as the smallest unit of weight (originally the weight of a plump, dry grain of wheat or barley from the middle of the ear). From late 14c as "roughness of surface; a roughness as of grains." In reference to wood, "quality due to the character or arrangement of its fibers," 1560s; hence, against the grain (1650), a metaphor from carpentry: cutting across the fibers of the wood is more difficult than cutting along them.

Earliest sense of the word in English was "scarlet dye made from insects" (early 13c.), a sense also in the Old French collateral form graine; see kermes for the evolution of this sense, which was frequent in Middle English; also compare engrain. In Middle English grain also could mean "seed of flowers; pip of an apple, grape, etc.; a berry, legume, nut." Grain alcohol attested by 1854.
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